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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.