Journal
SCIENCE CHINA-CHEMISTRY
Volume 63, Issue 8, Pages 1082-1090Publisher
SCIENCE PRESS
DOI: 10.1007/s11426-020-9768-x
Keywords
(3+2) cycloaddition; asymmetric catalysis; acylsilane; pyrrolidine; amino aldehyde; amino acids
Categories
Funding
- National Natural Science Foundation of China [21773051, 21702211, 21703051]
- Zhejiang Provincial Natural Science Foundation of China [LZ18B020001, LQ19B040001, LY18B020013]
- Hangzhou Science and Technology Bureau of China [20180432B05]
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The catalytic asymmetric synthesis of novel and chiral amino acid derivatives with unconventional chemo-, diastereo-, and enantio-selectivity remains a paramount challenge. Herein we reported a novel protocol for the use of highly enantioselective copper-catalyzed cycloaddition of alpha,beta-unsaturated acylsilanes as a springboard reaction for the facile synthesis of structurally diversified pyrrolidines and complicated alpha-amino esters by desilylation. The newly developed process could provide a wide range of synthetically useful acylsilane-substituted pyrrolidines (ASiP) in high yields and excellent diastereo- and enantio-selectivities with Cu/(R)-XylBINAP complex as the catalyst. And the downstream desilylation transformation enables to expand the potntial applications of 1,3-dipolar cycloaddition in the construction of structurally unique amino acid derivatives, in which an unprecedented and concerted fluoride anion-promoted C-X (X=H, Si, N, C) bond cleavage occurred to the enantioselective construction of aldehyde-substituted pyrrolidines, linear cinnamaldehyde or alkene-substituted amino esters in high ee values.
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