The Cyano Group as a Traceless Activation Group for the Intermolecular [3+2] Cycloaddition of Azomethine Ylides: A Five‐Step Synthesis of (±)‐Isoretronecanol | Zendy

Li Jundong | Zendy; Zhao Huaibo | Zendy; Jiang Xunjin | Zendy; Wang Xiance | Zendy; Hu Haiming | Zendy; Yu Lei | Zendy; Zhang Yandong | Zendy

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The Cyano Group as a Traceless Activation Group for the Intermolecular [3+2] Cycloaddition of Azomethine Ylides: A Five‐Step Synthesis of (±)‐Isoretronecanol

Author(s) -

Li Jundong,

Zhao Huaibo,

Jiang Xunjin,

Wang Xiance,

Hu Haiming,

Yu Lei,

Zhang Yandong

Publication year - 2015

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.201500961

Subject(s) - cycloaddition , sodium borohydride , chemistry , intermolecular force , azomethine ylide , combinatorial chemistry , group (periodic table) , pyrrolizidine , functional group , catalysis , 1,3 dipolar cycloaddition , organic chemistry , medicinal chemistry , stereochemistry , molecule , polymer

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.

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