Stereocontrolled Synthesis of Bicyclic Sulfamides via Pd-Catalyzed Alkene Carboamination Reactions. Control of 1,3-Asymmetric Induction by Manipulating Mechanistic Pathways

详细信息    查看全文

• 作者：Nicholas R. Babij ; Grace M. McKenna ; Ryan M. Fornwald ; John P. Wolfe
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：June 20, 2014
• 年：2014
• 卷：16
• 期：12
• 页码：3412-3415
• 全文大小：286K
• 年卷期：v.16,no.12(June 20, 2014)
• ISSN：1523-7052

文摘

A new annulation strategy for the synthesis of trans-bicyclic sulfamides is described. The Pd-catalyzed alkene carboamination reactions of 2-allyl and cis-2,5-diallyl pyrrolidinyl sulfamides with aryl and alkenyl triflates afford the fused bicyclic compounds in good yields and with good diastereoselectivity (up to 13:1 dr). Importantly, by employing reaction conditions that favor an anti-aminopalladation mechanism, the relative stereochemistry between the C3 and C4a stereocenters of the products is reversed relative to related Pd-catalyzed carboamination reactions that proceed via syn-aminopalladation.