Download PDF
Synfacts 2010(2): 0203-0203  
DOI: 10.1055/s-0029-1219101
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

A New C 2-Symmetric Imino Alcohol for Diethylzinc Additions to Aldehydes

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
P. Salehi*, M. Dabiri*, G. Kozehgary, M. Baghbanzadeh
Shahid Beheshti University, Tehran, Iran
Further Information

Publication History

Publication Date:
21 January 2010 (online)

    Permissions and Reprints

Significance

While enantioselective dialkylzinc additions to aldehydes are well developed, most protocols utilize a chiral amino alcohol ligand. In this report the authors have synthesized the chiral imino alcohol L1 in one step from 2-hydroxy-3-­pinaone and ethylenediamine. While this class of ligands has been applied before to these reactions, low asymmetric induction was obtained. However, L1 provides a variety of chiral secondary benzylic alcohols in excellent yields and enantio­selectivities.