Catalytic Asymmetric Cascade Using Spiro-Pyrrolidine Organocatalyst: Efficient Construction of Hydrophenanthridine Derivatives

Org Lett. 2017 Dec 15;19(24):6618-6621. doi: 10.1021/acs.orglett.7b03330. Epub 2017 Nov 28.

Abstract

A newly developed SPD (spiro-pyrrolidine) organocatalyst has been demonstrated to enable an asymmetric aza-Michael/Michael/aldol cyclization cascade, in which two six-membered rings (B/C) and three stereocenters have been constructed in a catalytic one-step process. It is so far the most efficient method for construction of hydrophenanthridine derivatives featuring high enantioselectivity. The trans- or cis-fused B/C-rings can be selectively assembled in a substrate-controlled manner. Moreover, this cascade could magnify to gram scale without loss of enanioselectivity.

Publication types

  • Research Support, Non-U.S. Gov't