Organocatalytic Enantioselective Vinylogous Aldol Reaction of Allyl Aryl Ketones to Activated Acyclic Ketones

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• 作者：Zhenzhong Jing ; Xiangbin Bai ; Wenchao Chen ; Gao Zhang ; Bo Zhu ; Zhiyong Jiang
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：January 15, 2016
• 年：2016
• 卷：18
• 期：2
• 页码：260-263
• 全文大小：455K
• ISSN：1523-7052

文摘

The first catalytic asymmetric vinylogous aldol reaction of activated allyls to activated acyclic ketones is disclosed. A variety of activated acyclic ketones, such as trifluoromethyl ketones, α-ketoesters, and α-keto phosphonates, were found to be involved forming diverse γ-selective aldol adducts with high enantioselectivities (up to >99% ee). The method provides an effective, general strategy to access valuable chiral electron-withdrawing group-substituted tertiary hydroxyl-based carboxylic acids.