Enantioselective Construction of Tetrahydroquinazoline Motifs via Palladium-Catalyzed [4 + 2] Cycloaddition of Vinyl Benzoxazinones with Sulfamate-Derived Cyclic Imines

Article abstract of DOI:10.1021/acs.orglett.8b00905

A palladium-catalyzed enantioselective [4 + 2] cycloaddition reaction of vinyl benzoxazinones with sulfamate-derived cyclic imines is described, affording the tetrahydroquinazolines bearing several functional rings in high yields (up to 99% yield) with good to excellent diastereoselectivities and excellent enantioselectivities (up to 96% ee). This reaction represents the first Pd-catalyzed asymmetric decarboxylative cycloaddition of vinyl benzoxazinones with imines.

Full text of DOI:10.1021/acs.orglett.8b00905

Letter
pubs.acs.org/OrgLett
Cite This: Org. Lett. XXXX, XXX, XXX−XXX
Enantioselective Construction of Tetrahydroquinazoline Motifs via
Palladium-Catalyzed [4 + 2] Cycloaddition of Vinyl Benzoxazinones
with Sulfamate-Derived Cyclic Imines
Chang Wang, Yan Li, Yang Wu, Qijun Wang, Wangyu Shi, Chunhao Yuan, Leijie Zhou, Yumei Xiao,
and Hongchao Guo*
Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. China
S
* Supporting Information
ABSTRACT: A palladium-catalyzed enantioselective [4 + 2]
cycloaddition reaction of vinyl benzoxazinones with sulfamate-
derived cyclic imines is described, affording the tetrahydro-
quinazolines bearing several functional rings in high yields (up
to 99% yield) with good to excellent diastereoselectivities and
excellent enantioselectivities (up to 96% ee). This reaction
represents the first Pd-catalyzed asymmetric decarboxylative cycloaddition of vinyl benzoxazinones with imines.
Scheme 1. Asymmetric Synthesis of Tetrahydroquinazolines
uinazolines are privileged scaffolds featured in many
Q natural and synthetic products. Many achiral and chiral
quinazoline derivatives show a wide range of biological activities
and pharmacological properties such as antibacterial, anti-
depressive, anti-inflammatory, and bronchodilator activities.1−6
Owing to the importance of the quinazoline derivatives, many
synthetic methods to achiral and chiral quinazolines have been
reported.7 However, examples on the enantioselective con-
struction of chiral tetrahydroquinazoline compounds are
extremely limited.8,9 In 2011, Gong reported a chiral phosphoric
acid catalyzed redox reaction of o-aminobenzoketones with
anilines, giving a series of tetrahydroquinazolines in high yields
and good enantioselectivities (Scheme 1).8a Two years later, they
demonstrated the combined catalysts of a gold complex and the
chiral phosphoric acid catalyzed cascade hydroamination/redox
reaction of ethynylphenyl-pyrrolidines with anisidines, affording
the tetrahydroquinazoline derivatives with excellent enantiose-
lectivity.8b Very recently, Xiao reported a practical one-pot Pd-
catalyzed hydroamination/Ru-catalyzed photoredox reaction for
preparation of chiral tetrahydroquinazolines.9 Although the
above-mentioned methods have been established for the
generation of chiral tetrahydroquinazoline motifs, developing
their new asymmetric synthetic method is still highly desirable.
The cycloaddition reactions utilizing palladium-stabilized
zwitterions have proven to be powerful tools for the construction
of heterocyclic compounds.10−16 Those palladium-stabilized
zwitterions are commonly generated in situ using a low valent
palladium catalyst and various allyl precursors such as
allylsilanes,10 vinyl cyclopropanes,11 γ-methylidene-δ-valerolac-
tones,12 vinylaziridines (or vinyloxazolidinones),13 vinyl epox-
ides (or vinylethylene carbonates),14 vinyl oxetanes,15 and vinyl
benzoxazinones.16 Among these allyl precursors, vinyl benzox-
azinones have been widely employed as C,N-1,4 synthons to
achieve [4 + n] annulation reactions since Tunge first reported
palladium-catalyzed [4 + 2] decarboxylative cycloadditions of 6-
vinyl-1,3-oxazinones and benzylidene malononitriles in 2006.16a
In 2008, Tunge also developed an asymmetric version of this
cycloaddition between vinyl benzoxazinones and benzylidene
malononitriles.16b In the past five years, the cycloddition
reactions involving vinyl benzoxazinones have intensively been
studied by Xiao, Glorius, Jorgensen, Lu, Shi, and Deng.16 Various
substrates including activated alkenes,16e sulfur ylides,16d,g
ketenes formed in stiu,16l methyleneindolinones,16k NHC-
homonenolates,16f,i iminium-ion activated α,β-unsaturated alde-
hydes,16h isatins,16j and mixed anhydrides formed in stiu16m have
proven to be compatible reaction partners in the asymmetric
Received: March 20, 2018
© XXXX American Chemical Society
A
DOI: 10.1021/acs.orglett.8b00905
Org. Lett. XXXX, XXX, XXX−XXX

Organic Letters
Letter
decarboxylative [4 + n] cycloaddition for synthesis of diverse
heterocyclic compounds. As part of our continued efforts on
asymmetric cycloaddition,17 herein, we report a palladium-
catalyzed highly stereoselective [4 + 2] cycloaddition reaction of
vinyl benzoxazinones with sulfamate-derived cyclic imines to
access chiral tetrahydroquinazolines.
To test the feasibility of the Pd-catalyzed [4 + 2] cycloaddition,
we initially investigated the model reaction of 4-vinylbenzox-
azinone 2a and sulfamate-derived cyclic imine 1a in dichloro-
methane at room temperature (Table 1). To our delight, under
After determining the optimized reaction conditions for the
reaction, we investigated the scope of the sulfamate-derived
cyclic imines 1 in the Pd-catalyzed asymmetric [4 + 2]
cycloaddition for the construction of chiral tetrahydro-
quinazoline motifs. As summarized in Table 2, this decarbox-
a
Table 2. Scope of Sulfamate-Derived Cyclic Imines 1
a
Table 1. Screening of the Reaction Conditions
b
c
d
entry
R
t/h
3
yield (%)
dr
ee (%)
1
6-Me (1b)
7-Me (1c)
7-i-Pr (1d)
6-t-Bu (1e)
7-t-Bu (1f)
8-t-Bu (1g)
6-OMe (1h)
7-OMe (1i)
8-OMe (1j)
7-F (1k)
2
3ba
3ca
3da
3ea
3fa
96
85
88
97
93
67
55
75
85
96
95
75
94
73
99
99
20:1
>20:1
16:1
95
96
94
96
93
92
92
95
94
91
88
93
95
91
91
94
2
2
3
4
4
3
14:1
5
3.5
5
15:1
6
3ga
3ha
3ia
16:1
7
2.5
2
19:1
8
>20:1
>20:1
>20:1
>20:1
19:1
9
3.5
2
3ja
b
c
d
10
11
12
13
14
15
16
3ka
3la
entry
ligand
solvent
t/h
yield (%)
dr
ee (%)
8-F (1l)
3
1
2
3
4
5
6
7
8
9
L1
L2
L3
L4
L2
L2
L2
L2
L2
L2
CH2Cl2
CH2Cl2
CH2Cl2
CH2Cl2
DCE
5
1.5
1.5
1.5
2
87
95
77
98
91
99
85
95
87
72
5:1
16:1
89
95
45
93
92
90
92
95
94
94
6-Cl (1m)
7-Cl (1n)
8-Cl (1o)
6-Br (1p)
7-Br (1q)
2
3ma
3na
3oa
3pa
3qa
2
>20:1
19:1
>20:1
15:1
2
5
>20:1
>20:1
>20:1
19:1
4
CHCl3
THF
2
a
Unless otherwise indicated, all reactions were carried out with 1 (0.1
mmol), 2a (0.15 mmol), Pd2(dba)3·CHCl3 (2.5 mol %), and chiral
2
14:1
toluene
AcOEt
toluene
2
>20:1
>20:1
>20:1
b
c
ligand L2 (7.5 mol %) in 1 mL of solvent. Isolated yield. Determined
by H NMR analysis. Determined by HPLC analysis using a chiral
stationary phase.
2
d
1
e
10
48
a
Unless otherwise indicated, all reactions were carried out with 1a (0.1
mmol), 2a (0.15 mmol), Pd2(dba)3·CHCl3 (2.5 mol %), and chiral
ligand L2 (7.5 mol %) in 1 mL of solvent. Isolated yield. Determined
by H NMR analysis. Determined by HPLC analysis using a chiral
stationary phase. 1 mol % Pd and 2.5 mol % ligand was used.
ylative [4 + 2] cycloaddition could offer the desired products in
moderate to excellent yields (55%−99%) with good to excellent
diastereo- and enantioselectivities (88%−96% ee). The reaction
was applicable to a variety of imines 1 bearing various
substituents on the different positions of the benzene ring,
regardless of whether an electron-donating or withdrawing group
on the benzene ring could be tolerated. Although 6-MeO-
substituted cyclic imine 1h led to a moderate 55% yield, excellent
diastereo- and enantioselectivity were still achieved in the
reaction (entry 7). The absolute configuration of the [4 + 2]
cycloadduct was unambiguously assigned as (8R, 13aR) through
X-ray crystallographic analysis of the product 3oa (CCDC
1830007).
Subsequent experiments were performed to evaluate the
generality of the reaction with respect to the vinyl benzoxazinone
2. As indicated in Table 3, various vinyl benzoxazinones 2
performed the palladium-catalyzed [4 + 2] cycloaddition to give
tetrahydroquinazolines in good to excellent yields with good to
excellent diastereo- and enantioselectivities (89−95% ee). Vinyl
benzoxazinones bearing an electron-withdrawing group dis-
played higher activity than the substrate having an electron-
donating group at the same position of the benzene ring (entry 2
vs 4, 3 vs 5). Additionally, a slight variation of the N-protecting
group on vinyl benzoxazinones was feasible. For example, the
substrate bearing an N-benzenesulfonyl group produced the
corresponding product in excellent yield with excellent stereo-
selectivity (entry 7).
b
c
d
1
e
catalysis of a complex of Pd2(dba)3·CHCl3 (2.5 mol %) and
axially chiral phosphoramidite ligand L1 (7.5 mol %), the [4 + 2]
cycloaddition proceeded smoothly to deliver the desired
cycloadduct in 87% yield with 89% ee, albeit in low
diastereoselectivity (dr = 5:1) (entry 1). Then, several axially
chiral phosphoramidite ligands were examined (entries 2−4).
The ligand L2 was found to be the optimal ligand for the reaction
in terms of diastereo- and enantioselectivity, affording the chiral
tetrahydroquinazoline derivative 3aa in 95% yield with 16:1 dr
and 95% ee (entry 2). With the use of chiral phosphoramidite L2
as the optimal chiral ligand, a quick screening of several solvents
including dichloromethane, 1,2-didhloroethane (DCE), CHCl3,
THF, toluene, and ethyl acetate (AcOEt) (entries 4−9) revealed
that toluene is the optimal solvent, leading to the [4 + 2]
cycloadduct 3aa in 95% yield with >20:1 dr and 95% ee (entry 8).
Decreasing the catalyst loading seemed to have no remarkable
influence on stereoselectivity, but sharply impaired the activity
(entry 10). Finally, the optimal reaction conditions were
determined as follows: with the use of Pd2(dba)3·CHCl3 (2.5
mol %) and chiral ligand L2 (7.5 mol %) as the catalyst in toluene
at room temperature.
B
DOI: 10.1021/acs.orglett.8b00905
Org. Lett. XXXX, XXX, XXX−XXX

Organic Letters
Letter
a
In conclusion, the Pd-catalyzed asymmetric [4 + 2] cyclo-
addition reaction of vinyl benzoxazinones with sulfamate-derived
cyclic imines has been developed for the enantioselective
construction of the tetrahydroquinazolines bearing several
functional rings. This is the first time imines were applied in a
Pd-catalyzed [4 + 2] cycloaddition reaction involving vinyl
benzoxazinones. The reaction could be performed on gram scale,
and further transformations of the cycloadducts provided other
useful chiral tetraquinazoline derivatives.
Table 3. Scope of Vinyl Benzoxazinones 2
b
c
d
entry
R/PG
t/h
3
yield (%)
dr
ee (%)
1
2
3
4
5
6
7
H/Ts (2a)
2
3
3
3
2
2
2
3aa
3ab
3ac
3ad
3ae
3af
95
84
88
93
91
97
98
>20:1
>20:1
>20:1
14:1
13:1
5:1
95
92
95
95
92
89
94
6-Me/Ts (2b)
7-Me/Ts (2c)
6-F/Ts (2d)
7-F/Ts (2e)
ASSOCIATED CONTENT
* Supporting Information
■
S
The Supporting Information is available free of charge on the
ACS Publications website at DOI: 10.1021/acs.orglett.8b00905.
6-OMe/Ts (2f)
H/PhSO2 (2g)
3ag
16:1
Experimental procedure, characterization data, HPLC
analysis data, NMR spectra, and X-ray crystallographic
data (PDF)
a
Unless otherwise indicated, all reactions were carried out with 1a (0.1
mmol), 2 (0.15 mmol), Pd2(dba)3·CHCl3 (2.5 mol %), and chiral
ligand L2 (7.5 mol %) in 1 mL of solvent. Isolated yield. Determined
by H NMR analysis. Determined by HPLC analysis using a chiral
stationary phase.
b
c
d
1
Accession Codes
CCDC 1830007 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge via
www.ccdc.cam.ac.uk/data_request/cif, or by emailing data_
request@ccdc.cam.ac.uk, or by contacting The Cambridge
Crystallographic Data Centre, 12 Union Road, Cambridge
CB2 1EZ, UK; fax: +44 1223 336033.
As shown in Scheme 2, the reaction on gram scale (0.55 g of
1a) was also performed to give the desired product in 93% yield
Scheme 2. Demonstration of Synthetic Utility
AUTHOR INFORMATION
■
Corresponding Author
*E-mail: hchguo@cau.edu.cn.
ORCID
Hongchao Guo: 0000-0002-7356-4283
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
This work is supported by the NSFC (21372256 and 21572264)
and the Program for Changjiang Scholars and Innovative
Research Team Project IRT1042.
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DOI: 10.1021/acs.orglett.8b00905
Org. Lett. XXXX, XXX, XXX−XXX