Organocatalytic Kinetic Resolution of Racemic Secondary Nitroallylic Alcohols Combined with Simultaneous Desymmetrization of Prochiral Cyclic Anhydrides

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• 作者：Suparna Roy ; Kan-Fu Chen ; Ramani Gurubrahamam ; Kwunmin Chen
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：October 3, 2014
• 年：2014
• 卷：79
• 期：19
• 页码：8955-8959
• 全文大小：284K
• ISSN：1520-6904

文摘

This study describes an organocatalytic kinetic resolution of racemic secondary nitroallylic alcohols (2) combined with simultaneous desymmetrization of prochiral cyclic anhydrides (1). The experimental results revealed that enantioselective alcoholysis of 3-substituted glutaric anhydrides afforded hemiesters (3) with high levels of enantioselectivities (up to 99% ee) in the presence of cinchonidine-derived thiourea catalyst (IV). The highly optical enrichment (up to 95% ee) of (S)-nitroallylic alcohols (2) was recovered.