Selective Cascade Reaction of Bisallenes via Palladium-Catalyzed Aerobic Oxidative Carbocyclization-Borylation and Aldehyde Trapping

Veluru Ramesh Naidu; Daniels Posevins; Chandra M R Volla; Jan-E Bäckvall

doi:10.1002/anie.201610524

Selective Cascade Reaction of Bisallenes via Palladium-Catalyzed Aerobic Oxidative Carbocyclization-Borylation and Aldehyde Trapping

Angew Chem Int Ed Engl. 2017 Feb 1;56(6):1590-1594. doi: 10.1002/anie.201610524. Epub 2017 Jan 9.

Authors

Veluru Ramesh Naidu¹, Daniels Posevins¹, Chandra M R Volla^{1

2}, Jan-E Bäckvall¹

Affiliations

¹ Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 10691, Stockholm, Sweden.
² Present address: Department of Chemistry, Indian Institute of Technology-Bombay, Powai, Mumbai, 400076, India.

PMID: 28067015
DOI: 10.1002/anie.201610524

Abstract

A cascade reaction, consisting of a palladium-catalyzed regioselective aerobic oxidative carbocyclization-borylation of bisallenes and a final aldehyde trapping, afforded triene alcohols with high diastereoselectivity. The cascade reaction occurs under mild reaction conditions and proceeds via an allylboron intermediate that is trapped by the aldehyde in a stereoselective manner.

Keywords: biomimetic oxidation; bisallene; cascade reaction; catalysis; palladium.

Publication types

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