Controllable Stereoselective Synthesis of (Z)- and (E)-Homoallylic Alcohols Using a Palladium-Catalyzed Three-Component Reaction

Yoshikazu Horino; Miki Sugata; Itaru Mutsuura; Keisuke Tomohara; Hitoshi Abe

doi:10.1021/acs.orglett.7b02979

Controllable Stereoselective Synthesis of (Z)- and (E)-Homoallylic Alcohols Using a Palladium-Catalyzed Three-Component Reaction

Org Lett. 2017 Nov 3;19(21):5968-5971. doi: 10.1021/acs.orglett.7b02979.

Authors

Yoshikazu Horino¹, Miki Sugata¹, Itaru Mutsuura¹, Keisuke Tomohara², Hitoshi Abe¹

Affiliations

¹ Graduate School of Science and Engineering, University of Toyama , 3190 Gofuku, Toyama 930-8555, Japan.
² Department of Hospital Pharmacy, University of Toyama , 2630 Sugitani, Toyama 930-0194, Japan.

PMID: 29064720
DOI: 10.1021/acs.orglett.7b02979

Abstract

Diastereoselective synthesis of (Z)- and (E)-homoallylic alcohols using a Pd-catalyzed three-component reaction of 3-(pinacolatoboryl)allyl benzoates, aldehydes, and aryl stannanes was developed, which provides an alternative method for the allylboration of aldehydes using α,γ-diaryl-substituted allylboronates. Both sets of reaction conditions enable access to either (Z)- or (E)-homoallylic alcohols with good to high alkene stereocontrol. The present method showed good functional group compatibility and generality. Efficient chirality transfer reactions to afford enantioenriched (Z)- and (E)-homoallylic alcohols were also achieved.

Publication types

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