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

Chemical Communications Pub Date: 2017-07-19 DOI: 10.1039/C7CC03010J

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 Br?nsted 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.

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