Exo-selective reductive macrocyclization of ynals

Organic Letters
Hengbin WangJohn Montgomery

Abstract

A general protocol for the highly exo-selective macrocyclization of ynals using a nickel/N-heterocyclic carbene catalyst system has been developed. A series of 10- to 21-membered macrocycles bearing an exomethylene substituent was synthesized in good yields with excellent regioselectivity (exo/endo >95:5). Very high levels of long-range diastereocontrol can also be achieved for some classes of macrocycles. Complementary to previously reported endo-selective macrocyclizations, this method provides accesses to exoalkylidene macrocycles from simple ynals in high selectivity.

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Citations

Aug 12, 2016·Journal of the American Chemical Society·Yu BaiMingji Dai
May 2, 2017·The Journal of Organic Chemistry·Sanjeewa K Rodrigo, Hairong Guan
Jun 18, 2017·Journal of the American Chemical Society·Hengbin WangJohn Montgomery
Jun 3, 2017·Science·Stephen K MurphySeth B Herzon
Jul 7, 2018·Natural Product Reports·Olivia GoetheSeth B Herzon

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