✦ LIBER ✦

Asymmetric cyclopropanation of chiral (1-dimethoxyphosphoryl-2-phenyl)vinyl p-tolyl sulfoxide: a new synthesis of enantiomerically pure 2-amino-3-phenyl-1-cyclopropane-phosphonic acid—a constrained analog of phaclofen

✍ Scribed by Wanda H Midura; Marian Mikołajczyk

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 292 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)00374-x

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✦ Synopsis

E-(S)-(1-Dimethoxyphosphoryl-2-phenyl)vinyl p-tolyl sulfoxide 3 was found to undergo cyclopropanation with sulfur ylides [dimethyl(oxo)sulfonium methylide, diphenyl sulfonium isopropylide and ethyl (dimethylsulfuranylidene)acetate (EDSA)] in a highly diastereoselective manner. The major diastereomer obtained in the reaction of E-(S)-3 with EDSA was converted into enantiopure (2R)-amino-(3R)-phenyl-(1R)-cyclopropane-phosphonic acid, a constrained analog of the GABA B antagonist, phaclofen.

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