Enantioselective Access to Chiral Cyclic Sulfamidates Through Iridium-Catalyzed Asymmetric Hydrogenation

Article abstract of DOI:10.1002/adsc.201801566

The Iridium-catalyzed asymmetric hydrogenation of cyclic sulfamidate imines was successfully developed with N-methylated ZhaoPhos L2 as the ligand. A variety of chiral cyclic sulfamidates were obtained with excellent results (up to 99% yield, 99% ee). Furthermore, this asymmetric hydrogenation can be employed as the key reaction step to prepare the important intermediates in organic synthesis. (Figure presented.).

Full text of DOI:10.1002/adsc.201801566

Title: Enantioselective Access to Chiral Cyclic Sulfamidates Through
Iridium-Catalyzed Asymmetric Hydrogenation
Authors: Yuanhua Liu, Yi Huang, Zhiyuan Yi, Gongyi Liu, Xiu-Qin
Dong, and Xumu Zhang
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10.1002/adsc.201801566
Advanced Synthesis & Catalysis
COMMUNICATION
DOI: 10.1002/adsc.201801566
Enantioselective Access to Chiral Cyclic Sulfamidates Through
Iridium-Catalyzed Asymmetric Hydrogenation
Yuanhua Liu,† Yi Huang,† Zhiyuan Yi,† Gongyi Liu,† Xiu-Qin Dong,*† Xumu
Zhang*‡,†
† Key Laboratory of Biomedical Polymers, Engineering Research Center of Organosilicon Compounds & Materials,
Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei, 430072, P. R.
China.
‡ Department of Chemistry and Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen,
Guangdong, 518055, P. R. China.
E-mail address: zhangxm@sustc.edu.cn; xiuqindong@whu.edu.cn.
Received: ((will be filled in by the editorial staff))
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/adsc.201######.((Please
delete if not appropriate))
sulfamidate imines have been regarded as important
access to chiral sulfamidates and derivatives.
Abstract.
The
Iridium-catalyzed
asymmetric
hydrogenation of cyclic sulfamidate imines was successfully
developed with N-methyled ZhaoPhos L2 as the ligand. A
variety of chiral cyclic sulfamidates were obtained with
excellent results (up to 99% yield, 99% ee). Furthermore,
this asymmetric hydrogenation can be employed as the key
reaction step to prepare the important intermediates in
organic synthesis.
Among these methods for the preparation of
chiral cyclic sulfamidates, the asymmetric
hydrogenation of prochiral cyclic sulfamidate imines
is one of the most convenient and outstanding
synthetic routes.[8] However, there is seldom highly
efficient catalytic system for the asymmetric
hydrogenation. In 2008, Zhou and co-workers
developed
Pd-catalyzed
enantioselective
Keywords: Asymmetric hydrogenation, cyclic sulfamidate
imine, chiral cyclic sulfamidate, enantioselectivity,
phosphorus ligand.
hydrogenation of cyclic sulfamidate ketimines with
excellent results.[8a] In continuation of our efforts to
develop the research field of asymmetric
hydrogenation, we are interested in exploring highly
efficient synthetic methods to construct chiral cyclic
sulfamidates through asymmetric hydrogenation.
Recently, our group developed privileged
bisphosphine-thiourea ligand, which exhibited
Chiral cyclic sulfamidates are versatile
intermediates for the construction of some important
chemical and biological molecules.[1-3] For example,
they have wide range of application to work as
potential precursors for the synthesis of chiral amines,
amino alcohols and amino acids through various
synthetic transformations.[2-3] Taking into account of
their great synthetic importance, much attention has
been paid to the development of highly efficient
synthetic methodologies. There are a limited number
of well-established asymmetric catalytic synthetic
methods in past decades.[4-11] The synthesis of chiral
cyclic sulfamidates have been developed mainly
through the intramolecular C–H amidation of
sulfamate esters catalyzed by transition metal-
complexes, such as Mn,[4] Ir,[5] Ru,[6] and Rh[7].
Asymmetric catalytic reduction of cyclic sulfamidate
imines including asymmetric hydrogenation[8] and
asymmetric transfer hydrogenation[9] is another
powerful approach for the construction of chiral cyclic
sulfamidates. In addition, Rh-catalyzed[10] or Pd-
catalyzed[11] asymmetric additions of substituted
boronic acids, boronates or borates to cyclic
powerful
performance
in
the
asymmetric
hydrogenation of some prochiral unsaturated
functionalized compounds.[12] High reactivity and
excellent stereoselective control capability could be
achieved through the possible hydrogen-bonding or
anion-binding interactions between the ligands and the
functional groups of substrates. Encouraged by these
excellent results, we herein successfully realized Ir/N-
methyled ZhaoPhos L2-catalyzed asymmetric
hydrogenation of cyclic sulfamidate imines, various
chiral cyclic sulfamidates were afforded with excellent
results (Scheme 1, up to 99% yield, 99% ee).
Scheme 1. Ir-catalyzed asymmetric hydrogenation of cyclic
sulfamate imines.
To explore the feasibility of Ir-catalyzed
1
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10.1002/adsc.201801566
Advanced Synthesis & Catalysis
asymmetric hydrogenation of cyclic sulfamidate
In order to achieve better enantioselectivity,
imines, 4-phenyl-5H-[1,2,3]-oxathiazole 2,2-dioxide the Ir/N-methylated ZhaoPhos ligand L2
-
1a[9b] was chosen as the model substrate to investigate
catalyzed asymmetric hydrogenation of 4-phenyl-
various bisphosphine ligands (Figure 1). As shown in 5H-[1,2,3]-oxathiazole 2,2-dioxide 1a was
Table 1, several bisphosphine-(thio)urea ligands L1- explored in different solvents. As shown in Table
L3 were applied in this Ir-catalyzed asymmetric
hydrogenation (Table 1, entries 1-3). ZhaoPhos L1
gave good enantioselectivity but with poor conversion
2, this catalytic system is solvent-dependent, the
solvents have great influence on the
enantioselectivity. Full conversions and moderate
a
(32% conversion, 82% ee, Table 1, entry 1). The N- enantioselectivities were obtained in MeOH and
methylated ZhaoPhos ligand L2 provided full EtOH (>99% cnversion, 68%-78% ee, Table 2,
conversion and excellent enantioselectivity (>99% entries 1-2). The nonpolar solvent hexane
conversion, 96% ee, Table 1, entry 2). The
bisphosphine-urea ligand L3 almost did not work in
provided
full
conversion
and
poor
enantioselectivity (>99% conversion, 49% ee,
this reaction (Table 1, entry 3). Very poor result was Table 2, entry 3). To our delight, excellent results
observed in the presence of ligand L4 without a were achieved in CH2Cl2, ClCH2CH2Cl, THF,
thiourea scaffold (Table 1, entry 4). Several other toluene, ethyl acetate and 1,4-dioxane (>99%
important chiral bisphosphine ligands, such as (S)- conversion, 90%-96% ee, Table 2, entries 4-9).
BINAP, (Rc, Sp)-DuanPhos and (S)-SegPhos, were
also inspected in this transformation, but poor
conversions and enantioselectivities were obtained
And CH2Cl2 provided the best result with >99%
conversion and 96% ee (Table 2, entry 4). When
the reaction temperature was decreased from 50
(Table 1, entries 5-7). Among these ligands, the N- °C to 25 °C, full conversion and 97% ee can be
methylated ZhaoPhos ligand L2 was proved to be the
best (Table 1, entry 2).
obtained (Table 2, entry 10).
Table 2. Screening solvents for the Ir/N-Me-ZhaoPhos
L2-catalyzed asymmetric hydrogenation of 4-phenyl-
5H-[1, 2, 3]oxathiazole 2,2-dioxide (1a).[a]
Table 1. Screening ligands for the Ir-catalyzed asymmetric
hydrogenation of 4-phenyl-5H-[1,2,3]-oxathiazole 2,2-
dioxide (1a).[a]
entry
solvent
conv. (%)[b]
ee (%)[c]
entry
ligand
L1
L2
L3
L4
conv. (%)[b]
ee (%)[c]
1
2
3
4
5
6
7
8
MeOH
EtOH
hexane
>99
>99
>99
>99
>99
>99
>99
>99
>99
>99
68
78
49
96
95
90
94
91
92
97
1
2
3
4
5
6
7
32
>99
trace
16
31
15
82
96
-
CH2Cl2
0
ClCH2CH2Cl
THF
(S)-BINAP
(Rc, Sp)-DuanPhos
(s)-SegPhos
33
29
16
toluene
22
ethyl acetate
1,4-dioxane
CH2Cl2
[a] Unless otherwise noted, all reactions were carried out
with a [Ir(COD)Cl]2/ligand/substrate 1a (0.1 mmol) ratio of
0.5:1.1:100 in 0.7 mL CH2Cl2 under 60 atm H2 at 50 °C in
24 h. The catalyst was pre-complexed in mixture solvents
MeOH/PhMe (V/V=1:3) at room temperature for 30 min
(0.1 mL for each reaction vial). The configuration of 2a was
determined by comparing the optical rotation data with
those reported in the literature.[8a, 9a, 9b]
9
10[d]
[a] Unless otherwise noted, all reactions were carried
out with a [Ir(COD)Cl]2/L2/substrate 1a (0.1 mmol)
ratio of 0.5:1.1:100 in 0.7 mL solvent under 60 atm H2
at 50 °C for 24 h. The catalyst was pre-complexed by
[Ir(COD)Cl]2 with ligand L2 in a 0.5:1.1 molar ratio in
mixture solvents MeOH/PhMe (V/V=1:3) at room
temperature for 30 min (0.1 mL for each reaction vial).
THF is tetrahydrofuran.
[b] Conversion was determined by 1H NMR analysis.
[c] Ee was determined by chiral HPLC analysis.
[b] Conversion was determined by 1H NMR analysis.
[c] Ee was determined by chiral HPLC analysis.
[d] Reaction temperature was 25 °C.
Having established the optimal reaction
conditions, we sought to investigate the general
substrate scope of this Ir/N-methylated ZhaoPhos
L2-catalyzed asymmetric hydrogenation of cyclic
sulfamidate imines. These reaction results were
summarized in Table 3. A variety of aryl
substituted cyclic sulfamate imines (1a
-1m) were
hydorgenated smoothly in this catalytic system,
the corresponding hydrogenation products (2a
2m) were obtained with full conversions, high
-
Figure 1. The structure of bisphosphine ligands.
2
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10.1002/adsc.201801566
Advanced Synthesis & Catalysis
yields and excellent enantioselectivities (94%-
99% yields, 92%-99% ee). Substrates with
different electronic substituents arranged in ortho-
, meta- or para-substitution patterns on the phenyl
ring have little effect on the reactivity and
As shown in Scheme 2, the gram-scale
asymmetric hydrogenation of 4-(3,5-difluorophenyl)-
5H-[1,2,3]-oxathiazole 2,2-dioxide 1h could be
performed well in the presence of 0.02 mol% (S/C = 5
000) Ir/N-methylated ZhaoPhos L2 catalyst, and the
desired product chiral cyclic sulfamidate 2h was
provided with excellent result (97% conversion, 94%
yield, TON = 4 700, 93% ee). The desired chiral cyclic
sulfamidate 2h is an important intermediate for the
construction of the enantiomer of piperazinone acid,
which was one of the two main molecular fragments
containing in clinical candidate MK-3207.[8b]
Moreover, the chiral cyclic sulfamidate 2h was easily
enantioselectivity,
which
were
smoothly
participated in the reaction. The cyclic sulfamate
imines containing electron-neutral (1a), electron-
donating (1b-1e), and electron-withdrawing (1f-
1m) substituents were hydrogenated well to give
the corresponding chiral cyclic sulfamidates with
excellent results. The 2-napthyl
(1n) and
heteroaromatic (1o) substrates worked well to
provide the desired products (2n 2o) with
-
reduced
by
LiAlH4
to
generate
(S)-
excellent results (>99% conversion, 97%-98%
yields, 96%-97% ee). In addition, the alkyl
substrate 4-benzyl-5H-[1,2,3]-oxathiazole 2,2-
dioxide (1p) could also be hydrogenated smoothly
to achieve full conversion, high yield and
moderate enantioselectivity (98% yield and 73%
ee).
difluorophenylglycinol in 92% yield and nearly
without loss of ee value (92% ee).[10h, 10l] The chiral
difluorophenylglycinol could be further derivatized to
work as new modulator of proteolytic processing of
the amyloid-β precursor proteins for Alzheimer’s
therapies.[13]
Table 3. Substrate scope study for the Ir-catalyzed
asymmetric hydrogenation of cyclic sulfamate imines.[a]
Scheme 2. Gram-scale Ir-catalyzed asymmetric
hydrogenation of 1h and synthetic transformation.
In summary, we successfully developed Ir-
catalyzed asymmetric hydrogenation of cyclic
sulfamidate imines with N-methylated ZhaoPhos L2
as the ligand, various chiral chiral cyclic sulfamidates
were obtained with excellent results (up to 99% yield,
99% ee). The gram-scale asymmetric hydrogenation
can be also proceeded well in the presence of 0.02
mol% (S/C = 5 000) the Ir/N-methylated ZhaoPhos L2
with 97% conversion, 94% yield and 93% ee.
Moreover, this highly efficient asymmetric
hydrogenation methodology exhibited excellent
synthetic utility, which can provide the important
intermediates for the construction of some important
organic molecules.
Experimental Section
[a] Unless otherwise noted, 0.1 mmol substrate 1, substrate
1/[Ir(COD)Cl]2/L2 = 1.0/0.005/0.011 at 25 oC under 60 atm
H2 in 0.7 mL CH2Cl2 for 24 h, and the catalyst was pre-
complexed by [Ir(COD)Cl]2 with L2 in a 0.5:1.1 molar ratio
in mixture MeOH/PhMe solvent (V/V=1:3) at room
temperature for 30 min (0.1 mL for each reaction vial).
Conversion was determined by H NMR analysis. Yield is
isolated yield. The ee value was determined by HPLC on a
chiral column.
[b] 72 h.
General procedure for the asymmetric hydrogenation
with S/C = 100: A stock solution was made by mixing
[Ir(COD)Cl]2 with N-methylated ZhaoPhos L2 in a 0.5:1.1
molar ratio in mixture solvent (MeOH/PhMe, V/V=1:3) at
room temperature for 30 min in a argon-filled glovebox. An
aliquot of the catalyst solution (0.1 mL, 0.001 mmol) was
transferred by syringe into the vials charged with different
substrates 1 (0.1 mmol for each) in the corresponding
anhydrous reaction solvent (0.7 mL). The vials were
subsequently transferred into an autoclave and the autoclave
was quickly purged with hydrogen gas for three times, then
was pressurized to the corresponding pressure of H2. The
1
3
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10.1002/adsc.201801566
Advanced Synthesis & Catalysis
reaction was stirred at the corresponding temperature for the
corresponding reaction time. After completed, the hydrogen
gas was released slowly and carefully. The solution was
concentrated and passed through a short column of silica gel
(eluant: EA) to remove the metal complex. The ee values of
hydrogenation products were determined by HPLC analysis
on a chiral stationary phase.
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Acknowledgements
We are grateful for financial support from the National
Natural Science Foundation of China (Grant No. 21432007,
21502145), the Wuhan Morning Light Plan of Youth Science and
Technology (Grant No. 2017050304010307), the Fundamental
Research Funds for Central Universities (Grant No.
2042018kf0202) and Shenzhen Nobel Prize Scientists Laboratory
Project (Grant No. C17783101). The Program of Introduc-ing
Talents of Discipline to Universities of China (111 Project) is also
appreciated.
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5
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10.1002/adsc.201801566
Advanced Synthesis & Catalysis
COMMUNICATION
Enantioselective Access to Chiral Cyclic
Sulfamidates Through Ir-Catalyzed Asymmetric
Hydrogenation
Adv. Synth. Catal. 2018, Volume, Page – Page
Yuanhua Liu,† Yi Huang,† Zhiyuan Yi,† Gongyi
Liu,† Xiu-Qin Dong,*† Xumu Zhang*‡,†
6
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