Novel Functional Hollow and Multihollow Organic Microspheres: Enhanced Efficiency in a Complex, Heterogeneous, Asymmetric, Three-Component/Triple Organocascade Reaction

Article abstract of DOI:10.1002/cctc.201601120

The pioneered construction of monodisperse hollow and multihollow J?rgensen–Hayashi-functionalized microspheres with a well-defined spherical morphology, high surface area, and large pore volume were developed by initial dispersion copolymerization of the J?rgensen–Hayashi organocatalyst with acrylamide and styrene monomers cross-linked by p-divinylbenzene and ethylene glycol dimethacrylate, respectively, on the surface of poly(styrene/acrylic acid) (PS) microspheres to form core–shell structures, followed by removal of the PS core by etching in organic solvents. The as-prepared hollow and multihollow microspheres were able to achieve better mass transfer in a complex heterogeneous asymmetric three-component/triple cascade reaction and provided the products in good yields (31–61 %) with excellent stereoselectivities (80:20–93:7 dr, >99 % ee).

Full text of DOI:10.1002/cctc.201601120

Accepted Article
Title: Novel functional hollow and multi-hollow organic microspheres:
enhanced efficiency in heterogeneous asymmetric three-
component/triple complex organocascade reaction
Authors: Fuqiang Dai, Zhiwei Zhao, Guangxin Xie, Dandan Feng, and
Xuebing Ma
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Link to VoR: http://dx.doi.org/10.1002/cctc.201601120
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10.1002/cctc.201601120
ChemCatChem
COMMUNICATION
Novel functional hollow and multi-hollow organic microspheres:
enhanced efficiency in heterogeneous asymmetric three-
component/triple complex organocascade reaction
Fuqiang Dai[a], Zhiwei Zhao[a], Guangxin Xie[a], Dandan Feng[a] and Xuebing Ma*[a]
Abstract: The pioneered construction of monodisperse hollow and
multi-hollow Jørgensen–Hayashi-functionalized microspheres with a
well-defined spherical morphology, high surface area and large pore
volume were developed by the first dispersion copolymerization of
Jørgensen–Hayashi organocatalyst with acrylamide and styrene mo-
nomers cross-linked by p-divinylbenzene and ethylene glycol dime-
thacrylate respectively on the surface of poly(styrene/acrylic acid)
(PS) microsphere to form the core-shelled structures, followed by the
removal of PS core by etching in organic solvents. The as-prepared
hollow and multi-hollow microspheres paved an exquisite strategy to
achieve better mass transfer in complex heterogeneous asymmetric
three-component/triple cascade reaction in good yields (31-61%)
and excellent stereoselectivities (80:20–93:7 dr, >99 %ee).
interest in hollow spheres owing to their outstanding features
with a well-defined structure, high specific surface area, low de-
nsity, abundant inner void, surface functionalization accessibility,
permeability and good compatibilities.[5] Up to now, the tremend-
ous efforts have been made in the fabrication of hollow-structur-
ed spheres with a controlled composition, tailored structure and
unique properties via hard-templating, soft-templating and temp-
late-free methods.[6] In the field of catalysis, these hollow-struct-
ured spheres enhanced the catalytic activity and stability of cata-
lyst owing to their protection against agglomeration and free acc-
ess for reactants to active catalytic sites in heterogeneous catal-
ysis,[7] such as metal catalysis,[8] photocatalysis,[9] acid catalysis
[10] and organocatalysis.[11] Among them, silica was generally us-
ed as a backbone for constructing hollow-structured shell. In fact,
the compatibility of catalyst support with reactants played an
important role in the mass transfer of reactants inside the inner
matrix of heterogeneous catalyst. Therefore, in view of enhance-
ed mass transfer resulted from the good compatibility of hollow-
structured organic shell, the development of functional hollow
organic microsphere containing robust organocatalyst is impera-
tive and highly desirable for successful heterogeneous multi-
component asymmetric organocascade reactions. To the best of
our knowledge, seldom was reported on the fabrication of hollow
organic microspheres applied in the field of catalysis.
Multi-component asymmetric organocatalytic cascade/domino
reactions with the advantages of high atom-economy, reduced
waste generation and synthetic efficiency have gained a great
deal of interest over the last decade as an effective tool for the
highly valuable construction of optically active complex molecu-
lar structures with multiple stereocenters relevant for pharma-
ceutical and natural products.[1] From the viewpoint of green che-
mistry, it is highly desirable for expensive organocatalyst to be
recovered and reused to achieve the perspective of economical
efficiency and sustainability in cascade/domino reactions by the
immobilization of organocatalysts onto various supports such as
polymers, inorganic silica and other metal oxides.[2] However,
the ever-reported successful heterogenization of homogeneous
star organocatalyst focused on relatively simple two-component/
double cascade reactions. For more complicated three-compon-
ent/triple cascade reaction, the harsher requirements appear to
place many significant and somewhat differing demands on the
characteristic of reaction environment, especially in heterogene-
ous catalytic phase. Unfortunately, the first heterogeneous three
-component Michael/Michael/aldol condensation triple cascade
reaction comprising a linear aldehyde, a nitroalkene and an a, β-
un-saturated aldehyde, catalyzed by crosslinked or pendant-fun-
ctionalized polystyrene[3] and acrylic polymer[4]-supported Jørge-
nsen–Hayashi catalyst, afforded optically active tetra-substituted
cyclohexene carbaldehydes with the disappointing catalytic res-
ults below 45% yield even for 7 days due to their intrinsic serious
mass transfer limitations for the fast movement of guest mole-
cules throughout the material.
Scheme 1. The schematic illustration of the heterogeneous hollow Poly(AA-
co-ProTMS) and multi-hollow Poly(AA-co-St-co-ProTMS) organocatalysts
The past two decades have witnessed the rapid growth of
In this communication, we reported the fabrication of a
novel class of monodisperse functional hollow and multi-hollow
organic microspheres bearing Jørgensen–Hayashi organocata-
[a]
Fuqiang Dai, Zhiwei Zhao, Guangxin Xie, Dandan Feng and
Xuebing Ma*
[12]
lyst [(S)-α, α-Bis(4-vinylphenyl)prolinol trimethylsilyl ether,
ProTMS]. Based on hard-template-assisted method, the well-
defined microspheres of ProTMS-functionalized hollow Poly(AA-
co-ProTMS) and multi-hollow Poly(AA-co-St-co-ProTMS) were
prepared via the first dispersion copolymerization of ProTMS
with acrylamide (AA) or AA and styrene (St) cross-linked res-
pectively by p-divinylbenzene (DVB) or ethylene glycol dimetha-
Key Laboratory of Applied Chemistry of Chongqing Municipality,
College of Chemistry and Chemical Engineering, Southwest
University, Chongqing, 400715, P. R. China
E-mail: zcj123@swu.edu.cn
Supporting information for this communication is given via a link at
the end of the document.
This article is protected by copyright. All rights reserved.

10.1002/cctc.201601120
ChemCatChem
COMMUNICATION
crylate (EGDMA) on the external surface of poly(styrene/ acrylic
acid) (PS) microspheres to form the core-shelled structure, and
then the further removal of PS core by etching in organic solv-
ents (Scheme 1).
(AA-co-St-co-ProTMS) exhibited the rough and highly smooth
surface, respectively.[14] After the removal of PS and St-selfpoly-
merized-nanospheres (< 5 nm) by etching in DMF, the Poly(AA-
co-St-co-ProTMS) microspheres with the multi-dimple-like con-
cave (Figure 1d) and multi-hollow interiors (Figure 1f) were con-
firmed by SEM and TEM images. Similarly, using DVB as a cro-
ss-linker in the absence of monomer St, the well-defined hollow
Poly(AA-co-ProTMS) (350–400 nm) with the THF-insoluble thin
shell (25–40 nm) comprised of the copolymer of ProTMS with
AA cross-linked by BVB was also constructed by the removal of
PS core using THF as an etchant (Figure 1e). Moreover, in order
to elucidate the enhanced catalytic efficiency promoted by men-
tioned-above hollow microspheres in multi-component/triple cas-
cade reaction, the Poly(St-co-ProTMS) copolymer with the nano-
sphere-interlinked morphology (Figure S2) was also prepared as
a control sample by the direct copolymerization of styrene and
ProTMS in emulsive aqueous ethanol solution (v/v = 5:4) at
70 °C for 10 h.
The loading capacity of organocatalyst ProTMS in poly(St-
co-ProTMS) was easily determined by elemental analysis to be
1.38 mmol g-1 on the basis of nitrogen content contained in
ProTMS (1.93%). Owing to nitrogen-contained monomer AA, the
gravimetric method by calcining the Poly(AA-co-ProTMS) and
Poly(AA-co-St-co-ProTMS) samples at 1000 °C was used as a
method to determine the loading capacities of ProTMS. Calculat-
ed from the mass of SiO2 converted from organic silicon under
oxygen atmosphere at high temperature, Poly(AA-co-ProTMS)
and Poly (AA-co-St-co-ProTMS) possessed 0.57 mmol g-1 and
0.54 mmol g-1 of ProTMS organocatalyst, respectively. From N2
adsorption-desorption isotherms (Table S2), the hollow Poly(AA-
co-ProTMS) (112.8 m2 g-1, 0.487 cc g-1) and multi-hollow Poly
(AA-co-St-co-ProTMS) (138.8 m2 g-1, 0.558 cc g-1) possessed
the higher BET-specific surface areas and pore volumes than
the core-shelled PS@poly(AA-co-ProTMS (56.1 m2 g-1 and
0.198 cc g-1) and PS@poly(AA-co-St-co-ProTMS) (73.4 m2 g-1
and 0.278 cc g-1), respectively. Unfortunately, the control sample
Poly(St-co-ProTMS) copolymer afforded the lowest BET-specific
surface area (13.1 m2 g-1) and pore volume (0.026 cc g-1). More-
over, the pore size distributions (PSDs) (Figure S5, ESI†) displ-
ayed the porous shell of hollow Poly(AA-co-ProTMS) and multi-
hollow Poly(AA-co-St-co-ProTMS), whose porous features were
required especially for the diffusion and transport of reactants
inside the active catalytic sites. It was noteworthy that the hollow
Poly(AA-co-ProTMS) possessed the non-uniform microporous
and mesoporous structures with the several peaks (0.7, 1.5, 1.9,
2.6, 4.8 and 8.0 nm) in the 0.5–10 nm range (Figure S5b, ESI†).
Delightedly, using EGDMA as a cross-linking agent, the shell of
the multi-hollow Poly(AA-co-St-co-ProTMS) exhibited the single
microporous structure (1.4 nm) with a narrow porous distribution
(Figure S5d, ESI†), which was different from the current hollow
spheres with the quasi-nonporous or highly disordered porous
shell.[15] Additionally, TGA showed that the multi-hollow Poly(AA-
co-St-co-ProTMS) contained 11.8% of adsorbed hydration water
from the mass loss below 150 °C. After the temperature reached
above 200 °C, a sharp weight loss of organic moieties (82.8%)
was observed (Figure S6, ESI†), which illustrated that the multi-
hollow Poly(AA-co-St-co-ProTMS) only remained thermally sta-
ble below 200 °C.
Figure 1. The SEM and TEM images of the core-shelled and hollow micro-
spheres: SEM of PS@poly(AA-co-ProTMS) (a), SEM of PS@poly(AA-co-St-
co-ProTMS) (b), SEM of hollow Poly(AA-co-ProTMS) (c), SEM of multi-hollow
Poly(AA-co-St-co-ProTMS) (d), TEM of hollow Poly(AA-co-ProTMS) (e) and
TEM of multi-hollow Poly(AA-co-St-co-ProTMS) (f).
The carboxyl-capping poly(styrene/acrylic acid) microsph-
eres with the hexagonal and uniform size of 350–400 nm (Figure
S1) were prepared by emulsifier-free copolymerizetion.[13] From
the SEM images shown in Figure 1a, b, the shell thickness of
core–shelled microspheres PS@poly(AA-co-St-co-ProTMS) and
PS@poly(AA-co-ProTMS) was measured in the range of ca. 30–
50 nm from the change of the diameter of particle in size, indica-
ting the formation of uniform organic outermost shell. Due to the
irregular aggregation of monomers and selective polymerization
cross-linked respectively by DVB and EGDMA, it was observed
that the core-shelled PS@poly(AA-co-ProTMS) and PS@poly
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10.1002/cctc.201601120
ChemCatChem
COMMUNICATION
In the proposed mechanism of three-component/triple
Michael/Michael/aldol condensation cascade reaction, the three-
step reaction begins with the first Michael addition of propion-
aldehyde enamine to nitrostyrene, further undergoes the second
Michael addition to the iminium derivative of cinnamaldehyde,
and then completes the intramolecular aldol cyclocondensation
of the resulting enamine to produce optically active tetra-substi-
tuted cyclohexene carbaldehydes.[16] Here, the whole reaction
process was monitored by HPLC. The peak area ratios (SP/SM)
of the peak area (SP) of final product (3S, 4S, 5R, 6R)-3-methyl-
5-nitro-4, 6-diphenylcyclohex-1-ene carbaldehyde to that (SM) of
reactant trans-β-nitrostyrene plotted versus reaction time (0–48
h) were used as the parameters to evaluate the catalytic activit-
ies of the copolymeric Poly(St-co-ProTMS), core-shelled PS@
poly(AA-co-St-co-ProTMS) and multi-hollow Poly(AA-co-St-co-
ProTMS).
ing the enhanced catalytic activity in the complex heterogeneous
cascade reaction.
From Figure 2, Poly(St-co-ProTMS) could not promote fa-
vourably the three-component triple cascade reaction only with
SP/SM = 0.18 for 48 h due to its severe mass transfer limitation of
the constrained steric environments resulted from the low surfa-
ce area (13.1 m2 g-1) and pore volume (0.026 cc g-1), although
Poly (St-co-ProTMS) possessed the highest loading capacity of
ProTMS organocatalyst (1.38 mmol g-1). Indeed, the first Michael
adduct of propylaldehyde to trans-β-nitrostyrene was isolated in
good yield (86%) with 98 %ee, indicating that the first Michael
adduct could be formed rapidly and then accumulated. However,
the further Michael addition to the iminium derivative of cinnama-
ldehyde was sterically hindered for the final product (< 5% yield)
owing to severe mass transfer limitation. By means of the pack-
age of ProTMS on the surface of PS microspheres, the core-
shelled PS@poly(AA-co-St-co-ProTMS) with the significantly im-
proved surface area (73.4 m2 g-1) and pore volume (0.278 cc g-1),
where most of active ProTMS were located on the external shell,
exhibited the increased catalytic activity with SP/SM = 2.3 for 48 h
due to the effective exposure of active ProTMS. Even so, the
final product was isolated in only 12% yield. The similar yield
(8%) for the core-shelled PS@poly(AA-co-ProTMS) was also
obtained. For this process to succeed, the somewhat differing
demands on the characteristics of catalytic environments should
be required in this complex heterogeneous three-component/tri-
ple cascade reaction. To our delight, after the removal of PS
core, the multi-hollow Poly(AA-co-St-co-ProTMS) with the high-
est surface area (138.8 m2 g-1) and pore volume (0.558 cc g-1) in
virtue of the most active catalytic sites showed the significantly
enhanced catalytic activity with SP/SM = 10.3 for 48 h (Table S3,
ESI†) and afforded the final product in 43% yield with the ex-
cellent stereoselectivity (89:11 dr, >99 %ee) similar as homoge-
neous ProTMS (46%, 89:11 dr, >99 %ee) (20 mol% of ProTMS
in toluene at 30 °C for 48 h. Similarly, the hollow Poly(AA-co-
ProTMS) (36%, 87:13 dr, 99 %ee) also displayed the more effe-
ctive catalytic activity than its corresponding core-shelled PS@
poly(AA-co-ProTMS) (8%, 86:14 dr, 99 %ee) (Table S4, ESI†).
Moreover, the further investigation of ever-reported MNPs Fe3O4
-supported ProTMS organocatalyst [12] gave the disappointed re-
sult (10% yield). On this basis, it was concluded that the multi-
hollow and hollow-structured morphology significantly improved
the pore volume and surface area of well-defined Poly(AA-co-
ProTMS) and Poly(AA-co-St-co-ProTMS) microspheres, and ev-
entually produced the more active and effective ProTMS, favor-
Figure 2. The peak area ratio profiles (SP/SM) of peak area (SP) of the final
product (3S, 4S, 5R, 6R)-3-methyl-5-nitro-4, 6-diphenylcyclohex-1-ene carbal-
dehyde to that (SM) of trans-β-nitrostyrene plotted versus reaction times during
whole reaction.
Table 1. Heterogeneous asymmetric three-component/triple organocascade
promoted by hollow Poly(AA-co-St-co-ProTMS) and Poly(AA-co-ProTMS).[a]
Entry
1
R1
R2
Yield (%)[b]
61
Dr[c]
%ee[d]
>99
Me
C6H5
91:9
55[e]
90:10
89:11
89:11
87:13
87:13
86:14
85:15
80:20
80:20
91:9
89:11
90:10
90:10
89:11
87:13
93:7
>99
>99
>99
>99
>99
>99
>99
>99
>99
>99
>99
>99
>99
>99
>99
>99
>99
>99
>99
>99
>99
>99
>99
2
Me
Et
4-MeOC6H5
C6H5
41
34[e]
55
3
51[e]
46
4
Me
i-Pr
Me
Me
Me
Me
n-Pr
Et
Furyl
43[e]
45
5
C6H5
40[e]
45
6
2-ClC6H5
3-ClC6H5
4-ClC6H5
4-BrC6H5
C6H5
41[e]
40
7
39[e]
35
8
34[e]
34
9
31[e]
60
92:8
10
11
12
80:20
80:20
89:11
89:11
87:13
85:15
51[e]
45
3-ClC6H5
2-ClC6H5
44[e]
53
Et
48[e]
[a] Poly(AA-co-St-co-ProTMS) (110 mg, 30 mol%), trans-β-nitrostyrene (0.2
mmol, 1.00 eq.), cinnamaldehyde (0.21 mmol, 1.05 eq.), aliphatic aldehyde
(0.24 mmol, 1.2 eq.), acetic acid (0.04 mmol) and DIPEA (0.06 mmol) in tolu-
ene (3 mL) at 30 °C for 48 h. [b] Yield of the isolated single, major diastereo-
isomer. [c] Determined by 1H NMR analysis of the crude reaction mixture. [d]
Determined by HPLC analysis of isolated single, major diastereoisomer on a
chiral phase. [e] Catalyzed by 30 mol% of poly(AA-co-ProTMS).
This article is protected by copyright. All rights reserved.

10.1002/cctc.201601120
ChemCatChem
COMMUNICATION
After the further optimization of catalytic conditions such as
solvent, temperature and dosage of catalyst in heterogeneous
Michael/Michael/aldol condensation cascade, the final product
(3S, 4S, 5R, 6R)-3-methyl-5-nitro-4, 6-diphenylcyclohex-1-ene
carbaldehyde in good yield (61%) with excellent stereoselectivity
(89:11 dr, >99 %ee) were finally achieved with 30 mol% of multi-
hollow Poly(AA-co-St-co-ProTMS) at 30 °C in toluene (3 mL) for
48 h. With the optimized conditions at hand, we set out to exa-
mine the scope of substrates promoted by multi-hollow Poly(AA-
co-St-co-ProTMS). As shown in Table 1, not only the linear alde-
hydes but also branched aldehydes could afford optically active
tetra-substituted cyclohexene carbaldehydes in the satisfactory
yields (34–61%) with the high diasteroselectivities (80:20–93:7
dr) and excellent enantioselectivities (>99 %ee). Especially, the
aromatic nitroalkenes bearing o-Cl substituent gave the higher
yields than those bearing m, p-Cl substituents (Entries 6–8, 11,
12). Furthermore, the hollow Poly(AA-co-ProTMS) afforded the
good diasteroselectivities (80:20–92:8 dr) and excellent enantio-
selectivities (>99 %ee), but slightly lower yields (31-55%) than
multi-hollow Poly(AA-co-St-co-ProTMS). Unfortunately, like hom-
ogeneous ProTMS, the Poly(AA-co-St-co-ProTMS) and Poly(AA
-co-ProTMS) microspheres catalyzed aliphatic nitroalkene to pr-
oduce the trace product, even for 72 h. Additionally, it was wor-
thwhile to note that the multi-hollow Poly(AA-co-St-co-ProTMS)
afforded the similar catalytic performance as the homogeneous
ProTMS.[16]
1/10) of carboxyl-capping PS (200 mg) containing PVA (0.5 wt%)
was also added. After well-dispersed, the ethanol solution (2.0
mL) containing ProTMS (150.0 mg, 0.4 mmol) and p-divinylben-
zene (DVB, 130.0 mg, 1.0 mmol) was injected and well-dispers-
ed under sonication. Finally, the aqueous solution (2 mL) of pot-
assium peroxydisulfate (40.0 mg, 0.15 mmol) was added by sy-
ringe. The resulting translucent emulsion was started by heating
up to 70 °C and carried out for 20 h under N2 atmosphere. The
solid PS@poly(AA-co-ProTMS) was separated by centrifugation,
washed with DI water (10 mL × 3) and ethanol (10 mL × 3). The
obtained PS@poly(AA-co-ProTMS) was dispersed in THF (20
mL) under sonication for 5 min and separated by centrifugation.
After treated three times in THF (20 mL), the primrose yellow
solid was washed with DI water (10 mL × 3), ethanol (10 mL × 3)
and dried under vacuum at 50 °C for 6 h to afford the hollow
Poly(AA-co-ProTMS) (410.5 mg).
Preparation of Poly(AA-co-St-co-ProTMS): To a N2 filled
three-necked flask (250 mL) was successively added AA (213.5
mg, 3.0 mmol), aqueous ethanol suspension (11 mL, v/v = 1/10)
of carboxyl-capping PS (250.0 mg) containing PVA (0.5 wt%)
and aqueous PVA solution (55 mL, 0.5 wt% of PVA). After well-
dispersed, the ethanol solution (3 mL) containing ethylene glycol
dimethacrylate (EGDMA, 148.5 mg, 0.75 mmol), styrene (104.3
g, 1.0 mmol) and ProTMS (75.0 mg, 0.2 mmol) was added drop-
wise and well-dispersed under sonication for 30 min. The resul-
ting translucent emulsion was heated to 80 °C and stirred for 24
h. The yellow solid PS@poly(AA-co-St-co-ProTMS) was separa-
ted by centrifugation and washed with DI water (10 mL × 3), eth-
anol (10 mL × 3). The obtained PS@poly(AA-co-St-co-Pro-TMS)
was treated by DMF (20 mL) under sonication for 5 min to remo-
ve the core PS and then separated by centrifugation. After dealt
with DMF (20 mL) three times, the primrose yellow solid was
washed with ethanol (10 mL × 3) and dried under vacuum at
After the completion of cascade reaction, the microsphere
Poly(AA-co-St-co-ProTMS) was recovered by centrifugation and
directly reused in the next run after being washed with ethyl
acetate (5 mL × 3). To our delight, the good diasteroselectivities
(85–91:15–9) and constant excellent stereoselectivity (99% ee)
could be achieved in five consecutive cycles of Poly(AA-co-St-
co-ProTMS). However, the isolated yields of final product gradu-
ally decreased from 61%, 58%, 54%, 49% to 48% in the fifth run, 50 °C for 6 h to afford the hollow Poly(AA-co-St-co-ProTMS)
which was probably attributed to the several factors including the
partially collapsed hollow structure (Figure S7, ESI†), irregular
pore distribution (Figure S8, ESI†) and decreased surface area
(32.1 m2 g-1), pore volume (0.203 cc g-1) resulted from the ad-
sorbed reactants and products.
(401.8 mg).
Acknowledgements
In conclusion, the fabrication of monodisperse ProTMS-fu-
nctionalized hollow and multi-hollow microspheres with the well-
defined morphology, high specific surface area and large pore
volume provided a strategy for solving catalytic efficiency of co-
mplex heterogeneous three-component/triple organocascade re-
action through the dramatic increase in effective catalytic sites.
We believe that the methodology of the enhanced catalytic effici-
ency by the hollow-structure for better mass transfer will benefit
more extensive applications in other complex heterogeneous ca-
scade reaction.
We gratefully acknowledge the support from the National
Science Foundation of China (21071116) and the Fundamental
Research Funds for the Central Universities (XDJK2015D028).
Keywords: Heterogeneous catalysis • Organocatalysis• Hollow
microsphere • Three-component/triple cascade reaction•
Enhanced catalytic efficiency
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COMMUNICATION
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This article is protected by copyright. All rights reserved.

10.1002/cctc.201601120
ChemCatChem
COMMUNICATION
COMMUNICATION
Fuqiang Da, Zhiwei Zhao, Guangxin Xie,
Dandan Feng and Xuebing Ma*
Page No. – Page No.
Novel functional hollow and multi-
hollow organic microspheres:
enhanced efficiency in
heterogeneous asymmetric three-
component/triple complex
organocascade reaction
The monodisperse Jørgensen–Hayashi catalyst-functionalized multi-hollow and
hollow microspheres with the well-defined spherical morphology and high surface
area enhanced complex heterogeneous three-component asymmetric triple
cascade reaction. The hollow microsphere exhibited the excellent stereoselectivity
in the fifth reuse
This article is protected by copyright. All rights reserved.