The P-Chiral Phosphane Ligand (MeO-BIBOP) for Efficient and Practical Large-Scale Rh-Catalyzed Asymmetric Hydrogenation of N-Acetyl Enamides with High TONs

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• 作者：Wenjie Li ; Sonia Rodriguez ; Adil Duran ; Xiufeng Sun ; Wenjun Tang ; Ajith Premasiri ; Jun Wang ; Kanwar Sidhu ; Nitinchandra D. Patel ; Jolaine Savoie ; Bo Qu ; Heewon Lee ; Nizar Haddad ; Jon C. Lorenz ; Larry Nummy ; Azad Hossain ; Nathan Yee ; Bruce Lu ; Chris H. Senanayake
• 刊名：Organic Process Research & Development
• 出版年：2013
• 出版时间：August 16, 2013
• 年：2013
• 卷：17
• 期：8
• 页码：1061-1065
• 全文大小：281K
• 年卷期：v.17,no.8(August 16, 2013)
• ISSN：1520-586X

文摘

A highly electron-rich P-chiral bis(trialkylphosphane) ligand MeO-BIBOP (1) was efficiently synthesized on large scale. The MeO-BIBOP鈥搑hodium complex exhibited remarkably high reactivities (up to 200,000 TON) for the hydrogenation of N-acetyl enamides to provide chiral acetamides on kilogram scale. In the meantime, a high-yielding, cost-effective, and practical preparation of N-acetyl enamide by reductive acylation of oxime was developed employing an in situ formation of Fe(II) acetate from Fe/AcOH/Ac₂O.