A rhodium(I)-xylyl-BINAP catalyzed asymmetric ynamide-[2 2 2] cycloaddition in the synthesis of optically enriched N,O-biaryls

作者：Oppenheimer Jossian; Johnson Whitney L; Figueroa Ruth; Hayashi Ryuji; Hsung Richard P^*

来源：Tetrahedron, 2009, 65(26): 5001-5012.

DOI：10.1016/j.tet.2009.03.078

• Aryl ynamides
• Asymmetric [2 2 2] cycloaddition
• Chiral N,O-biaryls
• Rhodium(I) catalyst and (S)-xylyl-BINAP
• C-N axial chirality
• double asymmetric induction of non-point stereocenters

A rhodium(I)-xylyl-BINAP catalyzed asymmetric [2 2 2] cycloaddition of achiral conjugated aryl ynamides with various diynes is described here. This asymmetric cycloaddition provides a series of structurally interesting chiral N,O-biaryls with excellent enantioselectivity along with a modest diastereoselectivity, with respect to both C-C and C-N axial chirality.

• 出版日期2009-6-27