An Organocatalytic Cope Rearrangement

Publisher： John Wiley & Sons Inc

E-ISSN： 1521-3757|128|38|11729-11733

ISSN： 0044-8249

Source： ANGEWANDTE CHEMIE, Vol.128, Iss.38, 2016-09, pp. : 11729-11733

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Abstract

AbstractThe first example of an organocatalytic Cope rearrangement is reported. Acyclic and cyclic acyl hydrazides catalyze the rearrangement of 1,5‐hexadiene‐2‐carboxaldehydes via iminium ion formation. A correlation between ring size and catalyst activity was observed for the cyclic hydrazides, with seven‐ and eight‐membered‐ring catalysts being the most active. Diazepane carboxylate 5 c (10 mol %) catalyzed the rearrangement of a range of dienes at room temperature in acetonitrile using triflic acid as a co‐catalyst. Preliminary proof of principle for asymmetric catalysis was provided by rearrangement of 3,3‐dimethyl‐7‐phenyl‐1,5‐heptadiene‐2‐carboxaldehyde in the presence of a novel 7‐substituted diazepane carboxylate.

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