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- Title
Manipulation of Spiroindolenine Intermediates for Enantioselective Synthesis of 3‐(Indol‐3‐yl)‐Pyrrolidines.
- Authors
Xia, Zi‐Lei; Zheng, Chao; Liang, Xiao‐Wei; Cai, Yue; You, Shu‐Li
- Abstract
By manipulating the reactivity of spiroindolenine species, a sequential Michael/retro‐Mannich/Mannich reaction of ω‐indol‐3‐yl α,β‐unsaturated ketones was developed. In the presence of 10 mol % of a chiral phosphoric acid as the catalyst, a series of 3‐(indol‐3‐yl)‐pyrrolidines were synthesized in high yields (up to 91 %) with excellent stereoselectivities (up to 92 % ee, >19:1 d.r.). The products obtained here undergo diverse functional‐group transformations. The mechanistic proposal of this reaction is supported by DFT calculations.
- Subjects
PYRROLIDINE synthesis; SPIRO compounds; INTERMEDIATES (Chemistry); ENANTIOSELECTIVE catalysis; CHEMICAL species; MANNICH reaction
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 4, p1170
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201812344