Tetrahedron Letters p. 3061 - 3065 (2002)
Update date:2022-07-30
Topics:
Midura, Wanda H
Miko?ajczyk, Marian
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 GABAB antagonist, phaclofen.
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