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- Title
The Cyano Group as a Traceless Activation Group for the Intermolecular [3+2] Cycloaddition of Azomethine Ylides: A Five-Step Synthesis of (±)-Isoretronecanol.
- Authors
Li, Jundong; Zhao, Huaibo; Jiang, Xunjin; Wang, Xiance; Hu, Haiming; Yu, Lei; Zhang, Yandong
- Abstract
The cyano group was used as a traceless activation group for the [3+2] cycloaddition of azomethine ylides in a two-step process, thereby providing a highly effective approach to 5-unsubstituted pyrrolidines. The transformation includes the silver acetate catalyzed intermolecular 1,3-dipolar cycloaddition of α-iminonitriles and an unprecedented sodium borohydride induced reductive decyanation reaction. A diverse array of substrates is amenable to this transformation. The methodology was further extended to a five-step total synthesis of the pyrrolizidine natural product isoretronecanol.
- Subjects
CYANO group; RING formation (Chemistry); SCHIFF bases; PYRROLIDINE; YLIDES
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 21, p6404
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201500961