A highly practical approach to chiral homoallylic–homopropargylic amines via aza-Barbier reaction. Issue 20 (18th May 2016)

• Record Type: Journal Article
• Authors: Yuan, Bin-Hua; Zhang, Zhi-Cheng; Liu, Wen-Jie; Sun, Xing-Wen
• Is Part Of: Tetrahedron letters. Volume 57:Issue 20(2016)
• Page Start: 2147
• Page End: 2151
• Publication Date: 2016-05-18
• Subjects: aza-Barbier reaction -- Homoallylic–homopropargylic amine -- N-tert-Butanesulfinyl imine; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.03.103
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: The first access to chiral homoallylic–homopropargylic amine bearing two contiguous stereocenters. A novel allylic bromide was illustrated in aza -Barbier reaction. Enantioenriched 3, 4-dihydro-2 H -pyrroles was prepared in high efficiency via 5- indo - dig pathway. Abstract: The first access to chiral homoallylic–homopropargylic amine bearing two contiguous stereocenters has been well accomplished via zinc-promoted aza -Barbier reaction. N - tert -Butanesulfinyl ketimines are well-tolerated substrates, providing the tertiary amines in high yields and with excellent diastereoselectivities. 3, 4-Dihydro-2 H -pyrroles could be prepared in high efficiency by cyclization of the corresponding amines.