Organocatalyzed Asymmetric 1,6-Conjugate Addition of para-Quinone Methides with Dicyanoolefins

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• 作者：Xuanyi Li ; Xiuyan Xu ; Weiwei Wei ; Aijun Lin ; Hequan Yao
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：February 5, 2016
• 年：2016
• 卷：18
• 期：3
• 页码：428-431
• 全文大小：421K
• ISSN：1523-7052

文摘

A chiral thiourea catalyzed asymmetric 1,6-conjugate addition of para-quinone methides with dicyanoolefins has been developed. The reaction provided an efficient approach to the synthesis of chiral diarylmethine skeletons in good yields (up to 99% yield) with high diastereo- and enantioselectivity (>20:1 dr and up to 99.5:0.5 er), also on a gram scale. The preliminary mechanistic study showed that the remote stereocontrol was achieved through intermolecular hydrogen-bond interaction between the chiral thiourea catalyst and the para-quinone methides directly for the first time.