Novel enantioselective synthesis of 1,3-butadien-2-ylmethanols via tandem alkylbromide-epoxide vinylations using dimethylsulfonium methylide.
[reaction: see text] 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.
Alcaraz
Lilian
L
Department of Medicinal Chemistry, AstraZeneca R&D Charnwood, Bakewell Road, Loughborough, Leics, LE11 5RH, UK. lilian.alcaraz@astrazeneca.com
Cox
Katherine
K
Cridland
Andrew P
AP
Kinchin
Elizabeth
E
Morris
James
J
Thompson
Stewart P
SP
D002070:Butadienes / Q000138:chemical synthesis*; D020650:Combinatorial Chemistry Techniques; D004852:Epoxy Compounds / Q000737:chemistry; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D000432:Methanol / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
D002070:Butadienes; D004852:Epoxy Compounds; D006842:Hydrocarbons, Brominated; D013452:Sulfonium Compounds; D014753:Vinyl Compounds; D000432:Methanol