Synthesis 2007(8): 1235-1241  
DOI: 10.1055/s-2007-965989
PAPER
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Synthesis of Enantioenriched Acetylenic 1,2-Amino Alcohols

Fabrice Chemla, Franck Ferreira*, Xavier Gaucher, Laëtitia Palais
Université Pierre et Marie Curie-Paris 6, Laboratoire de Chimie Organique (UMR CNRS 7611), Institut de Chimie Moléculaire (FR 2769), case 183, 4 place Jussieu, 75252 Paris Cedex 05, France
Fax: +33(0)144275571; e-Mail: franck.ferreira@upmc.fr;
Further Information

Publication History

Received 14 December 2006
Publication Date:
23 March 2007 (online)

Abstract

The stereoselective synthesis of enantioenriched anti- and syn-4-aminoalk-1-yn-3-ols is described. Initial reaction of racemic 3-(methoxymethoxy)allenylzinc with enantiopure Ellman’s (S S)-(tert-butylsulfinyl)imines was shown to give straightforward and highly stereoselective access to anti-(S S,3S,4R)-3-(methoxy­methoxy)-4-sulfinamidoalk-1-ynes. Upon treatment with dry methanolic hydrochloric acid at reflux, the latter led to the corresponding enantioenriched anti-(3S,4R)-4-aminoalk-1-yn-3-ols. Regarding the syn-diastereomeric (3R,4R)-4-aminoalk-1-yn-3-ols, they were obtained by ring opening of the corresponding cis-N-(tert-butylsulfinyl)aziridines by water under acidic conditions.