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Letter

Catalytic Asymmetric Synthesis with Rh−Diene Complexes: 1,4-Addition of Arylboronic Acids to Unsaturated Esters

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Jean-François Paquin, Corey R. J. Stephenson, Christian Defieber, and Erick M. Carreira*

Laboratorium fr Organische Chemie, ETH Hnggerberg, HCI H335, 8093 Zrich, Switzerland

Org. Lett., 2005, 7 (17), pp 3821–3824

DOI: 10.1021/ol051533l

Publication Date (Web): July 14, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, carreira@org.chem.ethz.ch

Abstract

A general route to enantioenriched tert-butyl 3,3-diarylpropanoates is presented. These useful building blocks are prepared via an asymmetric rhodium-catalyzed conjugate addition of arylboronic acids to unsaturated tert-butyl esters in the presence of chiral dienes as ligands. The addition of both electron-poor and electron-rich boronic acids proceeds smoothly with various enoates in 63−90% yield with high enantioselectivites (89−94% ee).

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Published In Issue August 18, 2005
Received June 30, 2005

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Letter

Catalytic Asymmetric Synthesis with Rh−Diene Complexes: 1,4-Addition of Arylboronic Acids to Unsaturated Esters

Abstract

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History

Recommend & Share

Related Content

Asymmetric Synthesis of 3,3-Diarylpropanals with Chiral Diene−Rhodium Catalysts

Catalytic Cycle of Rhodium-Catalyzed Asymmetric 1,4-Addition of Organoboronic Acids. Arylrhodium, Oxa-π-allylrhodium, and Hydroxorhodium Intermediates

Rhodium-Catalyzed Asymmetric 1,4-Addition of Aryl- and Alkenylboronic Acids to Enones

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