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The Baldwin Rearrangement: Synthesis of 2‐Acylaziridines
Author(s) -
Tangara Salia,
Kanazawa Alice,
Py Sandrine
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700920
Subject(s) - aziridine , chemistry , stereoselectivity , sigmatropic reaction , ring (chemistry) , stereochemistry , cope rearrangement , combinatorial chemistry , organic chemistry , catalysis
The Baldwin rearrangement is a thermally induced ring contraction of 4‐isoxazolines into 2‐acylaziridines. The reaction yields highly strained nitrogen‐containing three‐membered‐ring compounds from readily available five‐membered N‐O heterocycles. Diversely substituted isoxazolines are directly transformed into a variety of highly functionalized 2‐acylaziridines in a stereocontrolled process. In this review mechanistic aspects and stereoselectivity of this rearrangement are discussed. Although still undervalued, the Baldwin rearrangement may have significant applications in the synthesis of complex aziridine‐containing targets such as natural products or pharmaceuticals.