SF5-Enolates in Ti(IV)-Mediated Aldol Reactions

详细信息    查看全文

• 作者：Maksym V. Ponomarenko ; Simon Grabowsky ; Rumpa Pal ; Gerd-Volker Röschenthaler ; Andrey A. Fokin
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：August 5, 2016
• 年：2016
• 卷：81
• 期：15
• 页码：6783-6791
• 全文大小：480K
• 年卷期：0
• ISSN：1520-6904

文摘

The F···Ti bonding in the transition structures determines high trans- and syn-diastereoselectivities for aldol reactions of SF₅-acetates with aldehydes in the presence of TiCl₄ in the non-nucleophilic solvent CH₂Cl₂. Such bonding is canceled in nucleophilic solvents where opposite cis-stereochemistry is observed. The potential of thus obtained stereoisomeric SF₅-aryl acrylates as dipolarophiles in the preparation of SF₅-containing heterocycles is demonstrated.