InBr3-catalyzed direct alkynylation of nitrones with terminal alkynes: an efficient synthesis of N-hydroxy-propargyl amines

✍ Scribed by Du-Ming Ji; Ming-Hua Xu

• Publisher: Elsevier Science
• Year: 2009
• Tongue: French
• Weight: 704 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2009.03.206

✦ Synopsis

An InBr 3 -catalyzed direct and efficient alkynylation of nitrones with terminal alkynes was developed. The process enables practical synthesis of a wide range of synthetically useful N-hydroxy-propargyl amine derivatives in good yields under mild conditions. The application of this method to optically active propargylic N-hydroxyamines syntheses was also described. With chiral nitrones, good diastereoselectivities were obtained. Moreover, the first chiral indium(III) complex-catalyzed asymmetric alkynylation of nitrone was achieved with moderate enantioselectivity.