Enantioselective trapping of oxonium ylide intermediates by N-benzhydryl-α-imino ester: Synthesis of β-tetrasubstituted α-amino acids

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• 作者：Shi-Kun Jia ; Yu-Bing Lei ; Long-Long Song ; Shun-Ying Liu ; ^{syliu@sist.ecnu.edu.cn} ; Wen-Hao Hu ; ^{whu@chem.ecnu.edu.cn}
• 关键词：Three-component reaction ; Oxonium ylide ; N-Benzhydryl-α-imino ester ; β-Tetrasubstituted α-amino acids ; Chiral phosphoric acid
• 刊名：Chinese Chemical Letters
• 出版年：2017
• 出版时间：February 2017
• 年：2017
• 卷：28
• 期：2
• 页码：213-217
• 全文大小：882 K
• 卷排序：28

文摘

A synergistic rhodium(II)/phosphoric acid catalyzed three component reaction of 3-diazooxindoles, alcohols and N-benzhydryl-α-imino ester is developed for the efficient construction of chiral β-alkoxy Cβ-tetrasubstituted α-amino acid derivatives in good yields and with excellent diastereoselectivities and high enantioselectivities. The synthetic application of the resulting products was illustrated by reducing with Pd/C under H2 atmosphere followed reacting with CSCl2 at room temperature to rapid afford 3-spirocyclic oxindole in a good yield with a chirality retainment. The three-component reaction is proposed to proceed through an electrophilic trapping of the oxonium ylides by N-benzhydryl-α-imino ester.