Amine-promoted asymmetric [4+2] cycloadditions of α-acetoxymethyl allenoate and dual activated alkenes: stereoselective synthesis of poly-substituted cyclohexenes. Issue 25 (17th June 2015)

• Record Type: Journal Article
• Authors: Cheng, Mian; Liu, Jian-Kang; Tong, Xiaofeng; Tian, Ping
• Is Part Of: Tetrahedron letters. Volume 56:Issue 25(2015)
• Page Start: 3864
• Page End: 3867
• Publication Date: 2015-06-17
• Subjects: Allenoate -- Addition–elimination -- Dienamine -- [4+2] cycloaddition -- Cyclohexene; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.04.099
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: A chiral secondary amine-promoted asymmetric [4+2] cycloadditions of α-acetoxymethyl allenoate1 and electron-deficient alkenes2 have been developed. The reaction features the utilization of addition–elimination reaction between allenoate1 and the secondary amine to generate the key 2-aminobutadiene intermediate, which subsequently undergoes [4+2] cycloaddition with alkenes in a stepwise fashion, delivering the substituted cyclohexenes with good stereoselectivity.