Catalytic Asymmetric (4+3) Cyclizations of In Situ Generated ortho-Quinone Methides with 2-Indolylmethanols

Angew Chem Int Ed Engl. 2019 Jun 24;58(26):8703-8708. doi: 10.1002/anie.201901955. Epub 2019 May 17.

Abstract

The first catalytic asymmetric (4+3) cyclization of in situ generated ortho-quinone methides with 2-indolylmethanols has been established, which constructed seven-membered heterocycles in high yields (up to 95 %) and excellent enantioselectivity (up to 98 %). This approach not only represents the first catalytic asymmetric (4+3) cyclization of o-hydroxybenzyl alcohols, but also enabled an unprecedented catalytic asymmetric (4+3) cyclization of 2-indolylmethanols. In addition, a scarcely reported catalytic asymmetric (4+3) cyclization of para-quinone methide derivatives was accomplished.

Keywords: (4+3) cyclization; asymmetric catalysis; enantioselectivity; organocatalysis; ortho-quinone methide.

Publication types

  • Research Support, Non-U.S. Gov't