Synfacts 2006(10): 1049-1049  
DOI: 10.1055/s-2006-949314
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Indium-Mediated Synthesis of Homopropargylic Alcohols

Contributor(s): Paul Knochel, Andrei Gavryushin
L. C. Hirayama, K. K. Dunham, B. Singaram*
University of California at Santa Cruz, USA
Further Information

Publication History

Publication Date:
21 September 2006 (online)

Significance

The asymmetric addition of propargyl organometallics to aldehydes is a direct method for the preparation of chiral homopropargylic alcohols, which are valuable synthetic intermediates. Herein, a simple method of the enantioselective addition of organoindium compounds to aromatic and aliphatic aldehydes is reported. The reaction protocol is simple and the used chiral catalyst is commercially available; besides, it can be quantitatively recovered after the reaction. Good enantioselectivities (75-95%) were achieved with wide range of substrates.