Highly Selective Rhodium-Catalyzed Conjugate Addition Reactions of 4-Oxobutenamides

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• 作者：Jamie L. Zigterman ; Jacqueline C. S. Woo ; Shawn D. Walker ; Jason S. Tedrow ; Christopher J. Borths ; Emilio E. Bunel ; Margaret M. Faul
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：November 9, 2007
• 年：2007
• 卷：72
• 期：23
• 页码：8870 - 8876
• 全文大小：207K
• 年卷期：v.72,no.23(November 9, 2007)
• ISSN：1520-6904

文摘

jo701682cn00002>A variety of 4-oxobutenamides 1 were subjected to rhodium-catalyzed conjugate addition with arylboronicacids providing high regio- and enantioselectivity (97:3 to >99:1, >96% ee) and moderate to excellentyields (54-99%). The key to high selectivity is the use of sterically demanding P-chiral diphosphines,such as Tangphos or Duanphos. The product oxobutanamides 2 may be converted to alternate targets byselective derivatization of either the amide or ketone functional group. A stereochemical model predictingthe absolute sense of induction was developed based on single-crystal X-ray structures of product andprecatalyst.