Catalytic Enantioselective Allylations of Acetylenic Aldehydes via 2-Propanol-Mediated Reductive Coupling

Gilmar A Brito; Franco Della-Felice; Guoshun Luo; Alexander S Burns; Ronaldo A Pilli; Scott D Rychnovsky; Michael J Krische

doi:10.1021/acs.orglett.8b01776

Catalytic Enantioselective Allylations of Acetylenic Aldehydes via 2-Propanol-Mediated Reductive Coupling

Org Lett. 2018 Jul 6;20(13):4144-4147. doi: 10.1021/acs.orglett.8b01776. Epub 2018 Jun 25.

Authors

Gilmar A Brito^{1

2}, Franco Della-Felice^{1

2}, Guoshun Luo¹, Alexander S Burns³, Ronaldo A Pilli², Scott D Rychnovsky³, Michael J Krische¹

Affiliations

¹ Department of Chemistry , University of Texas at Austin , Austin , Texas 78712 , United States.
² Institute of Chemistry, University of Campinas (UNICAMP) , P.O. Box 6154, CEP, 13083-970 Campinas , São Paulo , Brazil.
³ Department of Chemistry , University of California at Irvine , 1102 Natural Sciences II , Irvine , California 92697 , United States.

Abstract

Cyclometalated π-allyliridium C,O-benzoates modified by ( S)-SEGPHOS or ( S)-Cl,OMe-BIPHEP catalyze enantioselective 2-propanol-mediated reductive couplings of diverse nonmetallic allyl pronucleophiles with the acetylenic aldehyde TIPSC≡CCHO. Absolute stereochemistries of the resulting secondary homoallylic-propargylic alcohols were assigned using Rychnovsky's competing enantioselective conversion method.

Publication types

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

Grants and funding

R01 GM069445/GM/NIGMS NIH HHS/United States