4
Tetrahedron
Levey, S.; Patrick, L.; Jordan-Hore, T. A.; Lee, A. L. Org. Lett.
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,
Figure 1. X-ray structure of 3dn
,
,
On the basis of the observed stereochemical outcome, the
chiral induction can be explained using the model shown in
Scheme 3. With the conformational preference, the chiral
oxazolidinone auxiliary plays a distinct role in providing a key
facial bias for the nucleophilic aryl group to approach from the
less hindered Re-face, provides the preferred diastereomer 3 as
illustrated.
,
1
7.
8.
9.
,
,
Liu, Y.; Li, D.; Park, C. M. Angew. Chem. Int. Ed. 2011, 50,
7333.
10. (a) Beenen, M. A.; Weix, D. J.; Ellman, J. A. J. Am. Chem.
Soc. 2006 128, 6304. (b) Jung, H. H.; Buesking, A. W.;
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12. (a) Zhi, W. B.; Li, J. Y.; Zou, D. P.; Wu, Y. S.; Wu, Y. J. J.
Org. Chem. 2017 82, 12286. (b) Zhi, W. B.; Li, J. Y.; Zou, D.
,
,
,
9
,
Scheme 3. A Proposed Stereochemical Model
P.; Wu, Y. S.; Wu, Y. J. Tetrahedron Lett. 2017, 59, 537.
13. (a) Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc.
1981, 103, 2127. (b) Evans, D. A.; Ennis, M D.; Mathre, D. J.
Conclusion
J. Am. Chem. Soc. 1982
, 104, 1737. (c) Evans, D. A.;
In summary,
diastereoselective conjugate addition for the synthesis of
optically active β-amino carbonyl compounds was developed by
a
high efficient palladium-catalyzed
Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1984, 106, 4261.
(d) Evans, D. A.; Chapman, K. T.; Hung, D. T. Angew. Chem.
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using
(S)-4-(tert-butyl)oxazolidin-2-one
and
(R)-2-
14. Gawley, R. E.; Rein, K.; Chemburkar, S. J. Org. Chem. 1989
54, 3002.
,
methylpropane-2-sulfinamide as chiral auxiliary, respectively. In
this protocol, water is used as the reaction solvent, which is
economical and green. Therefore, the present method provides a
novel and valuable strategy for the synthesis of diverse optically
active β-amino carbonyl compounds. In particular, (R)-2-
methylpropane-2-sulfinamide works well in this protocol as a
chiral auxiliary and the further study to improve the performance
with various substrates is underway in our lab.
15. Janey, J. M.; Iwama, T.; Kozmin, S. A.; Rawal, V. H. J. Org.
Chem. 2000, 65, 9059
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Y. Org. Lett. 2010, 12, 2356.
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Acknowledgments
We are grateful to the National Natural Science Foundation of
China (21172200, 21702191) for financial support.
18. Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002
35, 984.
,
19. Crystallographic data for the structure has been deposited with
the Cambridge Crystallographic Data Centre (CCDC 1584454).
See the Supporting Information for details. The absolute
configuration of other products was tentatively assigned by
analogy.
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