Enantioselective Synthesis of syn-伪-Aryl-尾-hydroxy Weinreb Amides: Catalytic Asymmetric Roskamp Reaction of 伪-Aryl Diazo Weinreb Amides

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• 作者：Sung Ho Shin ; Eun Hee Baek ; Geum-Sook Hwang ; Do Hyun Ryu
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：October 2, 2015
• 年：2015
• 卷：17
• 期：19
• 页码：4746-4749
• 全文大小：306K
• ISSN：1523-7052

文摘

A convenient one-pot procedure to synthesize a variety of highly optically active syn-伪-aryl-尾-hydroxy Weinreb amides using an asymmetric Roskamp/reduction strategy is described. An oxazaborolidinium ion catalyzed asymmetric Roskamp reaction of 伪-aryl diazo Weinreb amides with aldehydes produced 伪-phenyl-尾-keto Weinreb amides, which were in situ reduced with zinc borohydride to give syn-伪-aryl-尾-hydroxy Weinreb amides in good yields (up to 87%) with high enantioselectivities (up to 99% ee) and syn stereoselectivities (>20:1).