Origins of Selectivities in the Stork Diels-Alder Cycloaddition for the Synthesis of (±)-4-Methylenegermine

Xiao-Song Xue; Brian J Levandowski; Cyndi Qixin He; K N Houk

doi:10.1021/acs.orglett.8b02548

Origins of Selectivities in the Stork Diels-Alder Cycloaddition for the Synthesis of (±)-4-Methylenegermine

Org Lett. 2018 Oct 5;20(19):6108-6111. doi: 10.1021/acs.orglett.8b02548. Epub 2018 Sep 24.

Authors

Xiao-Song Xue^{1

2}, Brian J Levandowski², Cyndi Qixin He², K N Houk²

Affiliations

¹ State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Collaborative Innovation Center of Chemical Science and Engineering , Nankai University , Tianjin 300071 , China.
² Department of Chemistry and Biochemistry , University of California , Los Angeles , California 90095 , United States.

PMID: 30246539
DOI: 10.1021/acs.orglett.8b02548

Abstract

The remarkably high stereoselectivity of a Diels-Alder cycloaddition designed by Stork for the synthesis of germine has been examined with theory. We conceived a collaboration with Gilbert Stork, the great synthetic chemist and collaborator. We wished to complement Stork's insights with computations to explain the extraordinary selectivity he designed to introduce four new stereocenters in one step. Stork passed away on October 21, 2017, at age 95, sadly before we finished this work.

Publication types

Research Support, Non-U.S. Gov't