Novel Enantioselective Synthesis of 1,3-Butadien-2-ylmethanols via Tandem Alkylbromide-epoxide Vinylations Using Dimethylsulfonium Methylide

The treatment of chiral trans-disubstituted and trisubstituted 2,3-epoxy-1-bromides with an excess of dimethylsulfonium methylide 1 affords the corresponding 1,3-butadien-2-ylmethanols in good to excellent yields via a double one-carbon homologation.

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Published in:Organic letters 2005-03, Vol.7 (7), p.1399-1401
Main Authors: Alcaraz, Lilian, Cox, Katherine, Cridland, Andrew P, Kinchin, Elizabeth, Morris, James, Thompson, Stewart P
Format: Article
Language:English
Subjects:
Butadienes - chemical synthesis
Combinatorial Chemistry Techniques
Epoxy Compounds - chemistry
Hydrocarbons, Brominated - chemistry
Methanol - analogs & derivatives
Methanol - chemical synthesis
Molecular Structure
Stereoisomerism
Sulfonium Compounds - chemistry
Vinyl Compounds - chemistry
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cited_by cdi_FETCH-LOGICAL-a313t-6dff5f925f99086cdd60fb813442d6e3bbacc041c05d83ea3e02ded77c2039a03
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creator Alcaraz, Lilian
Cox, Katherine
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Kinchin, Elizabeth
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Thompson, Stewart P
description The treatment of chiral trans-disubstituted and trisubstituted 2,3-epoxy-1-bromides with an excess of dimethylsulfonium methylide 1 affords the corresponding 1,3-butadien-2-ylmethanols in good to excellent yields via a double one-carbon homologation.
doi_str_mv 10.1021/ol0502329
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Butadienes - chemical synthesis
Combinatorial Chemistry Techniques
Epoxy Compounds - chemistry
Hydrocarbons, Brominated - chemistry
Methanol - analogs & derivatives
Methanol - chemical synthesis
Molecular Structure
Stereoisomerism
Sulfonium Compounds - chemistry
Vinyl Compounds - chemistry
title Novel Enantioselective Synthesis of 1,3-Butadien-2-ylmethanols via Tandem Alkylbromide-epoxide Vinylations Using Dimethylsulfonium Methylide
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