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

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• 作者：Garrett Hoge
• 刊名：Journal of the American Chemical Society
• 出版年：2004
• 出版时间：August 18, 2004
• 年：2004
• 卷：126
• 期：32
• 页码：9920 - 9921
• 全文大小：52K
• 年卷期：v.126,no.32(August 18, 2004)
• ISSN：1520-5126

文摘

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.