Catalytic Asymmetric [4 + 1] Annulation of Sulfur Ylides with Copper–Allenylidene Intermediates

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• 作者：Qiang Wang ; Tian-Ren Li ; Liang-Qiu Lu ; Miao-Miao Li ; Kai Zhang ; Wen-Jing Xiao
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：July 13, 2016
• 年：2016
• 卷：138
• 期：27
• 页码：8360-8363
• 全文大小：391K
• 年卷期：0
• ISSN：1520-5126

文摘

The first copper-catalyzed asymmetric decarboxylative [4 + 1] cycloaddition of propargylic carbamates and sulfur ylides was successfully developed. This strategy led to a series of chiral indolines with synthetically flexible alkyne groups in good yields and with high enantio- and diastereoselectivities (up to 99% yield, 98% ee, and >95:5 dr). A possible mechanism and stereoinduction mode with copper–allenylidenes were proposed as the possible dipolar intermediate.