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.

Saved in:
Bibliographic Details
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
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0502329