Spirodiepoxides: Heterocycle synthesis and mechanistic insight

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

doi:10.1002/anie.200701401

Spirodiepoxides: Heterocycle synthesis and mechanistic insight

Stephen D. Lotesta, Sezgin Kiren, Ronald R. Sauers, Lawrence J. Williams

School of Arts and Sciences, Chemistry & Chemical Biology

Research output: Contribution to journal › Article › peer-review

27 Scopus citations

Abstract

(Chemical Equation Presented) 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.

Original language	English (US)
Pages (from-to)	7108-7111
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	46
Issue number	37
DOIs	https://doi.org/10.1002/anie.200701401
State	Published - 2007

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)

Keywords

Allenes
Nitrogen heterocycles
Reaction mechanism
Spirodiepoxides

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10.1002/anie.200701401

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abstract = "(Chemical Equation Presented) 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.",

keywords = "Allenes, Nitrogen heterocycles, Reaction mechanism, Spirodiepoxides",

author = "Lotesta, {Stephen D.} and Sezgin Kiren and Sauers, {Ronald R.} and Williams, {Lawrence J.}",

year = "2007",

doi = "10.1002/anie.200701401",

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journal = "Angewandte Chemie - International Edition",

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T2 - Heterocycle synthesis and mechanistic insight

AU - Lotesta, Stephen D.

AU - Kiren, Sezgin

AU - Sauers, Ronald R.

AU - Williams, Lawrence J.

PY - 2007

Y1 - 2007

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AB - (Chemical Equation Presented) 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.

KW - Allenes

KW - Nitrogen heterocycles

KW - Reaction mechanism

KW - Spirodiepoxides

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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ER -

Spirodiepoxides: Heterocycle synthesis and mechanistic insight

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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