Bimetallic Enantioselective Approach to Axially Chiral Allenes

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• 作者：Ruizhi L眉 ; Juntao Ye ; Tao Cao ; Bo Chen ; Wu Fan ; Weilong Lin ; Jinxian Liu ; Hongwen Luo ; Bukeyan Miao ; Shengjun Ni ; Xinjun Tang ; Nan Wang ; Yuli Wang ; Xi Xie ; Qiong Yu ; Weiming Yuan ; Wanli Zhang ; Can Zhu ; Shengming Ma
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：May 3, 2013
• 年：2013
• 卷：15
• 期：9
• 页码：2254-2257
• 全文大小：262K
• 年卷期：v.15,no.9(May 3, 2013)
• ISSN：1523-7052

文摘

An efficient bimetallic Zn(II)/Cu(I)-mediated asymmetric synthesis of simple axially chiral allenes from terminal alkynes and aldehydes was realized by taking advantage of the chiral amine (S)-伪,伪-diphenylprolinol 3. This one-pot procedure is compatible with broad scopes of both terminal alkynes and aldehydes, providing axially chiral allenes in practical yields with an excellent enantioselectivity. Control experiments revealed that CuBr is responsible for the efficient formation of propargylic amine while the combination of CuBr and ZnBr₂ plays crucial roles in the amine-to-allene transformation.