期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 38, 页码 11557-11561出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201606480
关键词
allylic strain; Cope rearrangements; hydrazides; iminium ions; organocatalysis
资金
- Natural Science and Engineering Research Council of Canada
- Canadian Institutes of Health Research
The 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 5c (10mol%) 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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