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Rh-Catalyzed Stereospecific Synthesis of Allenes from Propargylic Benzoates and Arylboronic Acids

Jonathan Ruchti and Erick M. Carreira*

*Laboratorium für Organische Chemie, ETH Zürich, HCI H335, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland, Email: carreiraorg.chem.ethz.ch

J. Ruchti, E. M. Carreira, Org. Lett., 2016, 18, 2174-2176.

DOI: 10.1021/acs.orglett.6b00793 (free Supporting Information)


Abstract

An enantiospecific approach to the synthesis of optically active, trisubstituted allenes from chiral propargylic benzoates and arylboronic acids is catalyzed by a complex formed in situ from [{Rh(cod)Cl}2] and a readily available phosphoramidite ligand. The method furnishes substituted allenes in high yields and excellent enantiospecificity under mild conditions.

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proposed mechanism



Key Words

allenes


ID: J54-Y2016