Journal
SCIENCE CHINA-CHEMISTRY
Volume 64, Issue 6, Pages 985-990Publisher
SCIENCE PRESS
DOI: 10.1007/s11426-021-9989-1
Keywords
N-heterocyclic carbene; organocatalysis; dynamic kinetic asymmetric transformation; 1-cyclopropylcarbaldehydes; asymmetric reactions
Categories
Funding
- National Natural Science Foundation of China [21772029, 21801051, 21961006, 22071036, 82360589, 81360589]
- The 10 Talent Plan (Shicengci) of Guizhou Province [[2016]5649]
- Guizhou Province Returned Oversea Student Science and Technology Activity Program [(2014)-2]
- Science and Technology Department of Guizhou Province [[2018]2802, [2019]1020]
- Program of Introducing Talents of Discipline to Universities of China (111 Program) at Guizhou University [D20023]
- Frontiers Science Center for Asymmetric Synthesis and Medicinal Molecules, Department of Education, Guizhou Province [Qianjiaohe KY (2020)004]
- Guizhou Province First-Class Disciplines Project [GNYL(2017)008]
- Guizhou University of Traditional Chinese Medicine (China)
- Guizhou University
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A novel N-heterocyclic carbene (NHC)-catalyzed enantioselective Mannich reaction of the remote gamma-carbon of cyclopropylcarbaldehydes is reported for the first time. The dynamic kinetic asymmetric transformation (DYKAT) process enables the generation of diastereo- and enantiomerically enriched multicyclic delta-lactam compound from 8 possible stereo-specific isomers. Multiple chiral functional molecules can be obtained from the lactam products through easy protocols while retaining their optical purities.
An N-heterocyclic carbene (NHC)-catalyzed enantioselective Mannich reaction of the remote gamma-carbon of cyclopropylcarbaldehydes is disclosed for the first time. Diastereo- and enantiomerically enriched multicyclic delta-lactam compound is afforded as the main product from 8 possible stereo-specific isomers through dynamic kinetic asymmetric transformation (DYKAT) processes. Multiple chiral functional molecules can be afforded from the lactam products through simple protocols with retentions of the optical purities.
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