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Catalytic enantioselective aza-Diels–Alder reactions of unactivated acyclic 1,3-dienes with aryl-, alkenyl-, and alkyl-substituted imines

Author:
Hatanaka, Yasuo, Nantaku, Shuuto, Nishimura, Yuhki, Otsuka, Tomoyuki, Sekikaw, Tohru
Source:
Chemical communications 2017 v.53 no.64 pp. 8996-8999
ISSN:
1364-548X
Subject:
Bronsted acids, catalysts, chemical reactions, enantioselectivity, imines
Abstract:
A catalytic enantioselective aza-Diels–Alder reaction of unactivated acyclic dienes with aryl-, alkenyl-, and alkyl-substituted imines is described. With 5–10 mol% loadings of a new Brønsted acid catalyst, the aza-Diels–Alder reaction of unactivated acyclic dienes proceeded to give the corresponding aza-Diels–Alder adducts in high yields (up to 98%) with excellent enantioselectivity (up to 98% ee). Preliminary DFT calculations suggest that the reaction proceeds through a chiral ion pair intermediate.
Agid:
6395988