Synlett 2015; 26(11): 1567-1572
DOI: 10.1055/s-0034-1380869
letter
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Reactions of Allylic Boronic Esters with Nucleophiles: Novel Umpolung Reactivity

Phillip J. Unsworth
School of Chemistry, University of Bristol, Cantock’s Close, Bristol, BS8 1TS, UK   Email: v.aggarwal@bristol.ac.uk
,
Lorenz E. Löffler
School of Chemistry, University of Bristol, Cantock’s Close, Bristol, BS8 1TS, UK   Email: v.aggarwal@bristol.ac.uk
,
Adam Noble
School of Chemistry, University of Bristol, Cantock’s Close, Bristol, BS8 1TS, UK   Email: v.aggarwal@bristol.ac.uk
,
Varinder K. Aggarwal*
School of Chemistry, University of Bristol, Cantock’s Close, Bristol, BS8 1TS, UK   Email: v.aggarwal@bristol.ac.uk
› Author Affiliations
Further Information

Publication History

Received: 23 March 2015

Accepted after revision: 07 May 2015

Publication Date:
20 May 2015 (online)


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Dedicated to Professor K. Peter C. Vollhardt with deep appreciation, where science and art combine

Abstract

Oxidative palladium-catalyzed reaction conditions have been developed to allow for regioselective and stereoselective coupling of allylic boronic esters with a range of carbon-, oxygen-, and nitrogen-based nucleophiles. Studies into the mechanism of the reaction have shown that the key transmetalation step occurs with retention of stereochemistry, since overall inversion is observed.

Supporting Information