Highly Enantioselective Preparation of Tertiary Alcohols and Amines by Copper‐Mediated Diastereoselective Allylic S_N2′ Substitutions

Abstract

Trisubstituted allylic pentafluorobenzoates react with diorganozinc reagents in the presence of CuCN⋅2 LiCl to provide alkenes bearing a chiral quaternary center in α position (>95 % ee). These alkenes are readily converted into chiral tertiary alcohols or into chiral amino alcohols by a straightforward sequence of ozonolysis followed by Curtius rearrangement (see scheme). Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2005/z500672_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.