Spirodiepoxides: Heterocycle Synthesis and Mechanistic Insight | Zendy

Lotesta Stephen D. | Zendy; Kiren Sezgin | Zendy; Sauers Ronald R. | Zendy; Williams Lawrence J. | Zendy

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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.

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