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Asymmetric Synthesis of Spirobenzazepinones with Atroposelectivity and Spiro‐1,2‐Diazepinones by NHC‐Catalyzed [3+4] Annulation Reactions
Author(s) -
Wang Lei,
Li Sun,
Blümel Marcus,
Philipps Arne R.,
Wang Ai,
Puttreddy Rakesh,
Rissanen Kari,
Enders Dieter
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201604819
Subject(s) - stereocenter , annulation , moiety , isatin , oxindole , chemistry , catalysis , cycloaddition , combinatorial chemistry , enantioselective synthesis , stereochemistry , organic chemistry
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.