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Spirodiepoxides: Heterocycle Synthesis and Mechanistic Insight
Author(s) -
Lotesta Stephen D.,
Kiren Sezgin,
Sauers Ronald R.,
Williams Lawrence J.
Publication year - 2007
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.200701401
Subject(s) - dimethyldioxirane , chemistry , amide , thioamide , reactivity (psychology) , nucleophile , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
In concert but out of sync : Reactions of spirodiepoxides (SDEs) with an amide, amidine, and thioamide and the first crystal structure of an SDE are reported (see scheme for reaction with amide; DMDO=2,2‐dimethyldioxirane). Nucleophilic SDE opening is rationalized in terms of a reactivity continuum involving the concerted, asynchronous opening of both epoxides, which is facilitated by coordination to the oxygen atom destined to become the hydroxy group.