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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201500961
Subject(s) - cycloaddition , chemistry , sodium borohydride , intermolecular force , combinatorial chemistry , azomethine ylide , functional group , 1,3 dipolar cycloaddition , pyrrolizidine , group (periodic table) , catalysis , medicinal chemistry , organic 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.