Stereochemical Prins cyclization: electronic versus steric effects on the synthesis of 2,4,6-trisubstituted tetrahydropyran rings

Kok Ping Chan; Ai Hua Seow; Teck Peng Loh

doi:10.1016/j.tetlet.2006.11.023

Stereochemical Prins cyclization: electronic versus steric effects on the synthesis of 2,4,6-trisubstituted tetrahydropyran rings

Kok Ping Chan, Ai Hua Seow, Teck Peng Loh

Nanyang Technological University

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

34 Scopus citations

Abstract

A convenient approach towards the synthesis of both syn- and anti-2,4,6-chlorotetrahydropyrans has been developed. The electronic and steric influences on the stereochemistry of the Prins cyclized products were investigated based on the substituents of the homoallylic alcohol.

Original language	English
Pages (from-to)	37-41
Number of pages	5
Journal	Tetrahedron Letters
Volume	48
Issue number	1
DOIs	https://doi.org/10.1016/j.tetlet.2006.11.023
State	Published - 1 Jan 2007
Externally published	Yes

Keywords

Lone-pair inductive effect
Prins cyclization
anti-Tetrahydropyran

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10.1016/j.tetlet.2006.11.023

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title = "Stereochemical Prins cyclization: electronic versus steric effects on the synthesis of 2,4,6-trisubstituted tetrahydropyran rings",

abstract = "A convenient approach towards the synthesis of both syn- and anti-2,4,6-chlorotetrahydropyrans has been developed. The electronic and steric influences on the stereochemistry of the Prins cyclized products were investigated based on the substituents of the homoallylic alcohol.",

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AU - Chan, Kok Ping

AU - Seow, Ai Hua

AU - Loh, Teck Peng

PY - 2007/1/1

Y1 - 2007/1/1

N2 - A convenient approach towards the synthesis of both syn- and anti-2,4,6-chlorotetrahydropyrans has been developed. The electronic and steric influences on the stereochemistry of the Prins cyclized products were investigated based on the substituents of the homoallylic alcohol.

AB - A convenient approach towards the synthesis of both syn- and anti-2,4,6-chlorotetrahydropyrans has been developed. The electronic and steric influences on the stereochemistry of the Prins cyclized products were investigated based on the substituents of the homoallylic alcohol.

KW - Lone-pair inductive effect

KW - Prins cyclization

KW - anti-Tetrahydropyran

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SN - 0040-4039

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Stereochemical Prins cyclization: electronic versus steric effects on the synthesis of 2,4,6-trisubstituted tetrahydropyran rings

Abstract

Keywords

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