Synfacts 2005(2): 0247-0247  
DOI: 10.1055/s-2005-916122
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Me2Zn-Mediated Addition of Acetylenes to Aldehydes and Ketones

Contributor(s): Paul Knochel, Andrei Gavryushin
P. G. Cozzi*, J. Rudolf, C. Bolm, P.-O. Norrby, C. Tomasini
Università di Bologna, Italy, and RWTH Aachen, Germany, and Technical University of Denmark, Lyngby, Denmark
Further Information

Publication History

Publication Date:
25 October 2005 (online)

Significance

Dimethylzinc was found to promote efficiently the addition reaction of terminal acetylenes to aldehydes and ketones leading to propargylic alcohols. A new, unprecedented mechanism of the zinc reagent activation is reported. The authors also performed an extensive computational work to back-up the obtained experimental results. The simplicity of the procedure and the good tolerance towards functional groups makes this method quite practical for synthetic applications.