Tandem intermolecular-intramolecular carbolithiation: application to the synthesis of silacyclopentanes

X D  Wei; R J K  Taylor

doi:10.1016/S0040-4039(03)01843-4

Tandem intermolecular-intramolecular carbolithiation: application to the synthesis of silacyclopentanes

X D Wei, R J K Taylor

Chemistry

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

Abstract

Silacyclopentanes have been prepared from vinyl(homoallyl)silanes or vinyl(liomopropargyl)silanes and organolithium reagents by a tandem intermolecular-intramolecular sequence involving a 5-exo cyclisation process. The unexpected stereochemical outcome of the sequence involving a 5-exo-dig cyclisation is rationalised. (C) 2003 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	7143-7146
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	38
DOIs	https://doi.org/10.1016/S0040-4039(03)01843-4
Publication status	Published - 15 Sept 2003

Keywords

SILICON-CARBON HETEROCYCLES
ORGANOLITHIUM ADDITIONS
STYRENE DERIVATIVES
ALKYLLITHIUMS
CYCLIZATION
SILACYCLES
LITHIUM

Access to Document

10.1016/S0040-4039(03)01843-4

Cite this

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title = "Tandem intermolecular-intramolecular carbolithiation: application to the synthesis of silacyclopentanes",

abstract = "Silacyclopentanes have been prepared from vinyl(homoallyl)silanes or vinyl(liomopropargyl)silanes and organolithium reagents by a tandem intermolecular-intramolecular sequence involving a 5-exo cyclisation process. The unexpected stereochemical outcome of the sequence involving a 5-exo-dig cyclisation is rationalised. (C) 2003 Elsevier Ltd. All rights reserved.",

keywords = "SILICON-CARBON HETEROCYCLES, ORGANOLITHIUM ADDITIONS, STYRENE DERIVATIVES, ALKYLLITHIUMS, CYCLIZATION, SILACYCLES, LITHIUM",

author = "Wei, {X D} and Taylor, {R J K}",

year = "2003",

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day = "15",

doi = "10.1016/S0040-4039(03)01843-4",

language = "English",

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journal = "Tetrahedron Letters",

issn = "0040-4039",

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T1 - Tandem intermolecular-intramolecular carbolithiation: application to the synthesis of silacyclopentanes

AU - Wei, X D

AU - Taylor, R J K

PY - 2003/9/15

Y1 - 2003/9/15

N2 - Silacyclopentanes have been prepared from vinyl(homoallyl)silanes or vinyl(liomopropargyl)silanes and organolithium reagents by a tandem intermolecular-intramolecular sequence involving a 5-exo cyclisation process. The unexpected stereochemical outcome of the sequence involving a 5-exo-dig cyclisation is rationalised. (C) 2003 Elsevier Ltd. All rights reserved.

AB - Silacyclopentanes have been prepared from vinyl(homoallyl)silanes or vinyl(liomopropargyl)silanes and organolithium reagents by a tandem intermolecular-intramolecular sequence involving a 5-exo cyclisation process. The unexpected stereochemical outcome of the sequence involving a 5-exo-dig cyclisation is rationalised. (C) 2003 Elsevier Ltd. All rights reserved.

KW - SILICON-CARBON HETEROCYCLES

KW - ORGANOLITHIUM ADDITIONS

KW - STYRENE DERIVATIVES

KW - ALKYLLITHIUMS

KW - CYCLIZATION

KW - SILACYCLES

KW - LITHIUM

U2 - 10.1016/S0040-4039(03)01843-4

DO - 10.1016/S0040-4039(03)01843-4

M3 - Article

SN - 0040-4039

VL - 44

SP - 7143

EP - 7146

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 38

ER -