期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 37, 页码 11110-11114出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201604819
关键词
1; 2-diazepinone; asymmetric synthesis; benzazepinone; N-heterocyclic carbene; spiro compound
A strategy for the NHC-catalyzed asymmetric synthesis of spirobenzazepinones, spiro-1,2-diazepinones, and spiro-1,2-oxazepinones has been developed via [3+4]-cycloaddition reactions of isatin-derived enals (3C component) with in-situ-generated aza-o-quinone methides, azoalkenes, and nitrosoalkenes (4atom components). The [3+4] annulation strategy leads to the seven-membered target spiro heterocycles bearing an oxindole moiety in high yields and excellent enantioselectivities with a wide variety of substrates. Notably, the benzazepinone synthesis is atroposelective and an all-carbon spiro stereocenter is generated.
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