Synfacts 2008(4): 0387-0387  
DOI: 10.1055/s-2008-1042787
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Gold-Mediated Substitution of Allylic Alcohols

Contributor(s): Mark Lautens, Frédéric Ménard
A. Aponick*, C.-Y. Li, B. Biannic
University of Florida, Gainesville, USA
Further Information

Publication History

Publication Date:
19 March 2008 (online)


Although nucleophilic addition to alkynes and allenes has been actively studied with gold catalysts recently, similar reactions with alkenes have received much less attention. The authors report that Au(I) and Au(III) can be used in ­intramolecular additions of oxygen nucleophiles to simple allylic alcohols. The reaction is synthetically equivalent to the hydroalkoxylation of allenes, with the advantage that the starting materials 1 are easier to prepare than the corresponding allenes. It is noteworthy that even in cases where the allylic alcohol was primary, no preactivation as a leaving group was needed (2a-d). The only byproduct of the reaction is water.