Continuum of mechanisms for nucleophilic substitutions of cyclic acetals

Jennifer R. Krumper; Walter A. Salamant; K. A. Woerpel

doi:10.1021/ol8019956

Continuum of mechanisms for nucleophilic substitutions of cyclic acetals

Jennifer R. Krumper, Walter A. Salamant, K. A. Woerpel

Chemistry

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

Abstract

(Chemical Equation Presented) The effect of nucleophile strength on diastereoselectivity in the nucleophilic substitution of cyclic acetals was explored. Stereoselectivity remained constant and high as nucleophilicity increased until a threshold value was reached. Beyond this point, however, selection of Lewis acid determined whether stereochemical inversion or erosion was observed.

Original language	English (US)
Pages (from-to)	4907-4910
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	21
DOIs	https://doi.org/10.1021/ol8019956
State	Published - 2008

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol8019956

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abstract = "(Chemical Equation Presented) The effect of nucleophile strength on diastereoselectivity in the nucleophilic substitution of cyclic acetals was explored. Stereoselectivity remained constant and high as nucleophilicity increased until a threshold value was reached. Beyond this point, however, selection of Lewis acid determined whether stereochemical inversion or erosion was observed.",

author = "Krumper, {Jennifer R.} and Salamant, {Walter A.} and Woerpel, {K. A.}",

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AU - Salamant, Walter A.

AU - Woerpel, K. A.

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AB - (Chemical Equation Presented) The effect of nucleophile strength on diastereoselectivity in the nucleophilic substitution of cyclic acetals was explored. Stereoselectivity remained constant and high as nucleophilicity increased until a threshold value was reached. Beyond this point, however, selection of Lewis acid determined whether stereochemical inversion or erosion was observed.

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Continuum of mechanisms for nucleophilic substitutions of cyclic acetals

Abstract

ASJC Scopus subject areas

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