The first asymmetric synthesis of alpha-sulfanylphosphonates.
[reaction: see text] Diastereoselectivity of up to 88% was achieved for the synthesis of an alpha-mercapto gamma-unsaturated phosphonate using the readily available chiral dimenthylphosphonyl ester group and a carbanionic [2,3]-sigmatropic rearrangement. Absolute configuration of the newly formed chiral center of this nonracemic thiol was determined, and the corresponding phosphono thiolane and thiolane S-oxide were also stereoselectively prepared.
Marchand
P
P
Laboratoire de Chimie Moléculaire et Thio-organique, UMR 6507-ISMRA-Université de Caen, 6 Bd du Maréchal Juin 14050 Caen Cedex, France.
Gulea
M
M
Masson
S
S
Saquet
M
M
Collignon
N
N
D000890:Anti-Infective Agents / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D063065:Organophosphonates / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013876:Thiophenes / Q000138:chemical synthesis*
D000890:Anti-Infective Agents; D063065:Organophosphonates; D013876:Thiophenes