Divergent diastereoselectivity in the addition of nucleophiles to tetrahydrofuran-derived oxonium ions

Jared T. Shaw; K. A. Woerpel

doi:10.1016/S0040-4020(99)00441-X

Divergent diastereoselectivity in the addition of nucleophiles to tetrahydrofuran-derived oxonium ions

Jared T. Shaw, K. A. Woerpel

Chemistry

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

Abstract

Alkyl substituted lactol acetates have been found to undergo highly stereoselective substitution reactions mediated by tin (IV) bromide. The highest selectivity is observed in the case of 4,4-di-isopropyl, 2-methyl substitution in which the selectivity depends on the nucleophile. Allyltrimethylsilane adds with high (95:5) 1,2-syn selectivity while 2- methyl-trimethylsiloxy propene adds with high (>98:2) anti selectivity. These results can be rationalized through conformational analysis of the oxonium ion intermediate.

Original language	English (US)
Pages (from-to)	8747-8756
Number of pages	10
Journal	Tetrahedron
Volume	55
Issue number	29
DOIs	https://doi.org/10.1016/S0040-4020(99)00441-X
State	Published - Jul 16 1999

Keywords

Carbenium ions
Furans

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(99)00441-X

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title = "Divergent diastereoselectivity in the addition of nucleophiles to tetrahydrofuran-derived oxonium ions",

abstract = "Alkyl substituted lactol acetates have been found to undergo highly stereoselective substitution reactions mediated by tin (IV) bromide. The highest selectivity is observed in the case of 4,4-di-isopropyl, 2-methyl substitution in which the selectivity depends on the nucleophile. Allyltrimethylsilane adds with high (95:5) 1,2-syn selectivity while 2- methyl-trimethylsiloxy propene adds with high (>98:2) anti selectivity. These results can be rationalized through conformational analysis of the oxonium ion intermediate.",

keywords = "Carbenium ions, Furans",

author = "Shaw, {Jared T.} and Woerpel, {K. A.}",

year = "1999",

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T1 - Divergent diastereoselectivity in the addition of nucleophiles to tetrahydrofuran-derived oxonium ions

AU - Shaw, Jared T.

AU - Woerpel, K. A.

PY - 1999/7/16

Y1 - 1999/7/16

N2 - Alkyl substituted lactol acetates have been found to undergo highly stereoselective substitution reactions mediated by tin (IV) bromide. The highest selectivity is observed in the case of 4,4-di-isopropyl, 2-methyl substitution in which the selectivity depends on the nucleophile. Allyltrimethylsilane adds with high (95:5) 1,2-syn selectivity while 2- methyl-trimethylsiloxy propene adds with high (>98:2) anti selectivity. These results can be rationalized through conformational analysis of the oxonium ion intermediate.

AB - Alkyl substituted lactol acetates have been found to undergo highly stereoselective substitution reactions mediated by tin (IV) bromide. The highest selectivity is observed in the case of 4,4-di-isopropyl, 2-methyl substitution in which the selectivity depends on the nucleophile. Allyltrimethylsilane adds with high (95:5) 1,2-syn selectivity while 2- methyl-trimethylsiloxy propene adds with high (>98:2) anti selectivity. These results can be rationalized through conformational analysis of the oxonium ion intermediate.

KW - Carbenium ions

KW - Furans

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SN - 0040-4020

VL - 55

SP - 8747

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JO - Tetrahedron

JF - Tetrahedron

IS - 29

ER -

Divergent diastereoselectivity in the addition of nucleophiles to tetrahydrofuran-derived oxonium ions

Abstract

Keywords

ASJC Scopus subject areas

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