Asymmetric Synthesis of Spirobenzazepinones with Atroposelectivity and Spiro-1,2-Diazepinones by NHC-Catalyzed [3+4] Annulation Reactions
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- 作者：Dr. Lei Wang ; Sun Li ; Marcus Blü ; mel ; Arne R. Philipps ; Ai Wang ; Dr. Rakesh Puttreddy ; Prof. Dr. Kari Rissanen and Prof. Dr. Dieter Enders
- 刊名：Angewandte Chemie
- 出版年：2016
- 出版时间：September 5, 2016
- 年：2016
- 卷：128
- 期：37
- 页码：11276-11280
- 全文大小：1947K
- ISSN：1521-3757
文摘
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.