Synfacts 2006(5): 0494-0494  
DOI: 10.1055/s-2006-934427
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Construction of Deoxypropionate Chains via Asymmetric Carboalumination

Contributor(s): Paul Knochel, Andrei Gavryushin
B. Liang, T. Novak, Z. Tan, E. Negishi*
Purdue University, West Lafayette, USA
Further Information

Publication History

Publication Date:
21 April 2006 (online)

Significance

This is a new and the first really catalytic method for the synthesis of a deoxypoly­propionate chain and related chiral compounds. Such motif is ubiquitous in many useful natural products, possessing biological activity. This catalytic approach relies on the Zr-catalyzed asymmetric carboalumination of allylic alcohols, followed by carefully designed synthetic transformations. Using this new method, rather complex functionalized deoxypropionate molecules became available from inexpensive starting materials in a short simple synthetic sequence.