Enantioselective Synthesis of Fused Polycyclic Tropanes via Dearomative [3 + 2] Cycloaddition Reactions of 2-Nitrobenzofurans.

Enantioselective Synthesis of Fused Polycyclic Tropanes via Dearomative [3 + 2] Cycloaddition Reactions of 2-Nitrobenzofurans.

Wang, Zhen;Wang, Dong-Chao;Xie, Ming-Sheng;Qu, Gui-Rong;Guo, Hai-Ming;
Organic letters 2020 Vol. 22 pp. 164-167
255
wang2020enantioselectiveorganic

Abstract

A straight synthetic approach to fused polycyclic tropane scaffold formation through an asymmetric dearomatization cycloaddition process of 2-nitrobenzofurans with cyclic azomethine ylides was successfully developed. In the presence of a chiral copper complex, derived from Cu(OAc) and a diphosphine ligand, a series of fused polycyclic tropane derivatives were obtained in high yields (75-91%) with excellent enantioselectivities (90-98%). The utility of this method was showcased by the facile transformation of product.

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