期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 48, 页码 17189-17193出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201908896
关键词
amine catalysis; cyclic beta-amino acid; Michael addition; Michael donors; remote gamma carbon
资金
- National Natural Science Foundation of China [21772029, 21562012, 21762012, 21801051]
- National Key Technologies RD Program [2014BAD23B01]
- Thousand Talent Plan
- 10 Talent Plan (Shicengci) of Guizhou Province
- S&T Planning Project of Guizhou Province [[2017]1402, [2017]5788]
- Department of Science and Technology of Guizhou Province [[2019]1020]
- Guizhou Province Returned Oversea Student Science and Technology Activity Program, Guizhou University
- Guizhou Province First-Class Disciplines Project (Yiliu Xueke Jianshe Xiangmu) [GNYL(2017)008]
- Guizhou University of Traditional Chinese Medicine (China)
- Open Fund of Guizhou Key Laboratory of Miao Medicine [QMYY[2017]101]
- Singapore National Research Foundation [NRF-NRFI2016-06]
- Ministry of Education of Singapore [MOE2013-T2-2-003, MOE2016-T2-1-032, RG108/16]
- A*STAR Individual Research Grant [A1783c0008]
- Nanyang Research Award Grant
Disclosed herein is a new catalytic approach for an efficient access to cyclic beta-amino acids widely found in bioactive small molecules and peptidic foldamers. Our method involves addition of the remote gamma-carbon atoms of alpha,beta-unsaturated imines to enals by iminium organic catalysis. This highly chemo- and stereo-selective reaction affords cyclic beta-amino aldehydes that can be converted to amino acids bearing quaternary stereocenters with exceptional optical purities. Our study demonstrates the unique power of organic catalytic remote carbon reactions in rapid synthesis of functional molecules.
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