Remote-stereocontrolled (3+2)-annulation of pyrrolidinone-based MBH carbonates with 2-arylideneindane-1,3-diones

Abstract

With the assistance of a chiral phosphine catalyst, a remote-controlled enantioselective (3+2)-annulation between pyrrolidinone-based Morita-Baylis-Hillman (MBH) carbonates and 2-arylideneindane-1,3-diones has been successfully realized under mild conditions. This reaction efficiently constructs chiral spiro[cyclopenta[b]pyrrole-6,2'-inden]-3-yl)acrylates with high efficiency and enantioselectivity. Notably, the asymmetric transformation proceeds through the selective activation of the Cε and Cε′ positions of the pyrrolidinone-based MBH carbonates.