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Manipulation of Spiroindolenine Intermediates for Enantioselective Synthesis of 3‐(Indol‐3‐yl)‐Pyrrolidines
Author(s) -
Xia ZiLei,
Zheng Chao,
Liang XiaoWei,
Cai Yue,
You ShuLi
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201812344
Subject(s) - enantioselective synthesis , reactivity (psychology) , mannich reaction , chemistry , phosphoric acid , catalysis , functional group , combinatorial chemistry , organocatalysis , organic chemistry , reaction conditions , medicine , polymer , alternative medicine , pathology
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.