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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Bibliographic Details
Published inOrganic letters Vol. 7; no. 7; pp. 1399 - 1401
Main Authors Alcaraz, Lilian, Cox, Katherine, Cridland, Andrew P, Kinchin, Elizabeth, Morris, James, Thompson, Stewart P
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 31.03.2005
Amer Chemical Soc
Subjects
Butadienes - chemical synthesis
Chemistry
Chemistry, Organic
Combinatorial Chemistry Techniques
Epoxy Compounds - chemistry
Hydrocarbons, Brominated - chemistry
Methanol - analogs & derivatives
Methanol - chemical synthesis
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
Sulfonium Compounds - chemistry
Vinyl Compounds - chemistry
HOMOLOGATED ALLYLIC ALCOHOLS
ORGANIC-SYNTHESIS
CROSS-METATHESIS
DIELS-ALDER REACTIONS
AQUEOUS-MEDIA
CARBONYL-COMPOUNDS
ALDEHYDES
GENERATION
REGIOSELECTIVE BUTA-1,3-DIENYLATION
CYTOTOXIC CLERODANE DITERPENOIDS
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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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0502329