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Gold Meets Rhodium: Tandem One-Pot Synthesis of β-Disubstituted Ketones via Meyer-Schuster Rearrangement and Asymmetric 1,4-Addition

Max M. Hansmann, A. Stephen K. Hashmi* and Mark Lautens*

*Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada, Email: hashmihashmi.de, mlautenschem.utoronto.ca

M. M. Hansmann, A. S. K. Hashmi, M. Lautens, Org. Lett., 2013, 15, 3226-3229.

DOI: 10.1021/ol4011739


Abstract

The compatibility of two metal complexes (Au/Rh) and their orthogonal ligand systems (NHC/diene) in a bimetallic catalytic system enables an asymmetric one-pot tandem Au/Rh-catalyzed synthesis of highly enantioenriched β-disubstituted ketones starting from racemic propargyl alcohols.


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Key Words

Meyer-Schuster Rearrangement, 1,4-addition


ID: J54-Y2013