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Stereoselective Cyclization and Pyramidal Inversion Strategies for P-Chirogenic Phospholane Synthesis

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posted on 18.08.2004, 00:00 by Garrett Hoge
Preparation of P-chirogenic mono- and bisphospholanes is reported. The demonstrated method employs a stereoselective cyclization of cyclic sulfates with primary phosphines in the presence of base to generate “cis” or “cis/cis” P-chirogenic phospholanes followed by heat-induced pyramidal inversion to provide “trans” or “trans/trans” P-chirogenic phospholanes. A rhodium complex of one “trans/trans” phospholane is applied to the highly enantioselective asymmetric hydrogenation of a substrate precursor to the pharmaceutical candidate pregabalin.