Phenyl versus Ethyl Transfer in the Addition of Organozinc Reagents to Aldehydes: A Theoretical Study

Abstract

The dramatic improvement in diphenylzinc addition to aldehydes that is obtained by adding diethylzinc was investigated by DFT methods. The strong preference for phenyl over ethyl transfer can be understood in terms of overlap with the phenyl π system in the transition state (see picture). Reasons for the high ee value in the presence of Et2Zn are discussed. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2003/z51150_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.