Highly selective formation of propargyl- and allenyltrichlorosilanes and their regiospecific addition to various types of aldehydes: preparation of both allenic and homopropargylic alcohols

U  Schneider; M  Sugiura; S  Kobayashi

doi:10.1016/j.tet.2005.08.114

Highly selective formation of propargyl- and allenyltrichlorosilanes and their regiospecific addition to various types of aldehydes: preparation of both allenic and homopropargylic alcohols

U Schneider, M Sugiura, S Kobayashi

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

Abstract

The highly selective preparation of propargyl- and allenyltrichlorosilanes via metal-catalyzed silylation of propargyl chloride has been developed. These trichlorosilyl nucleophiles were then shown to add to various types of aldehydes to afford the corresponding allenic and homopropargylic alcohols, respectively, in high yields with complete regiospecificity. Remarkably, these carbon-carbon bond-forming reactions simply proceeded in N,N-dimethylform amide (DNIF) without using any metal catalysts. (c) 2005 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	496-502
Number of pages	7
Journal	Tetrahedron
Volume	62
Issue number	2-3
DOIs	https://doi.org/10.1016/j.tet.2005.08.114
Publication status	Published - 9 Jan 2006

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10.1016/j.tet.2005.08.114

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abstract = "The highly selective preparation of propargyl- and allenyltrichlorosilanes via metal-catalyzed silylation of propargyl chloride has been developed. These trichlorosilyl nucleophiles were then shown to add to various types of aldehydes to afford the corresponding allenic and homopropargylic alcohols, respectively, in high yields with complete regiospecificity. Remarkably, these carbon-carbon bond-forming reactions simply proceeded in N,N-dimethylform amide (DNIF) without using any metal catalysts. (c) 2005 Elsevier Ltd. All rights reserved.",

author = "U Schneider and M Sugiura and S Kobayashi",

year = "2006",

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doi = "10.1016/j.tet.2005.08.114",

language = "English",

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AU - Schneider, U

AU - Sugiura, M

AU - Kobayashi, S

PY - 2006/1/9

Y1 - 2006/1/9

N2 - The highly selective preparation of propargyl- and allenyltrichlorosilanes via metal-catalyzed silylation of propargyl chloride has been developed. These trichlorosilyl nucleophiles were then shown to add to various types of aldehydes to afford the corresponding allenic and homopropargylic alcohols, respectively, in high yields with complete regiospecificity. Remarkably, these carbon-carbon bond-forming reactions simply proceeded in N,N-dimethylform amide (DNIF) without using any metal catalysts. (c) 2005 Elsevier Ltd. All rights reserved.

AB - The highly selective preparation of propargyl- and allenyltrichlorosilanes via metal-catalyzed silylation of propargyl chloride has been developed. These trichlorosilyl nucleophiles were then shown to add to various types of aldehydes to afford the corresponding allenic and homopropargylic alcohols, respectively, in high yields with complete regiospecificity. Remarkably, these carbon-carbon bond-forming reactions simply proceeded in N,N-dimethylform amide (DNIF) without using any metal catalysts. (c) 2005 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.tet.2005.08.114

DO - 10.1016/j.tet.2005.08.114

M3 - Article

SN - 0040-4020

VL - 62

SP - 496

EP - 502

JO - Tetrahedron

JF - Tetrahedron

IS - 2-3

ER -

Highly selective formation of propargyl- and allenyltrichlorosilanes and their regiospecific addition to various types of aldehydes: preparation of both allenic and homopropargylic alcohols

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