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Synlett 2006(7): 1039-1042  
DOI: 10.1055/s-2006-939063
LETTER
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Ring-Opening of N-tert-Butanesulfinylaziridines: Access to Acetylenic α-Amino Alcohols

Laëtitia Palais, Fabrice Chemla, Franck Ferreira*
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(1)44277567; e-Mail: franck.ferreira@upmc.fr;
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Publication History

Received 13 February 2006
Publication Date:
24 April 2006 (online)

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Abstract

Ring-opening of enantiopure trans and cis 2,3-disubstituted ethynyl N-tert-butanesulfinylaziridines by water under acidic conditions proved to be highly regio- and diastereoselective, leading to the corresponding enantiopure anti and syn acetylenic α-amino alcohols. The regio- and stereochemistries were unambiguously determined by NOE experiments through the formation of oxazol­idinone derivatives.

Key words

amino alcohols - asymmetric synthesis - aziridines - dia­stereoselectivity - regioselectivity

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Acetylenic α-Amino Alcohols 4a-g; Typical Procedure. A stirred solution of N-tert-butanesulfinylaziridines 3a-g (1.00 mmol) and PTSA monohydrate (190 mg, 1.00 mmol) in MeCN (40 mL) and H2O (5.7 mL) was refluxed for 20 h. After cooling to r.t., a sat. aq solution of NaHCO3 (40 mL) and CH2Cl2 (40 mL) were added and the resulting mixture was stirred for 15 min at r.t. The layers were then separated and the aqueous layer was extracted with CH2Cl2 (3 × 40 mL). The combined organic layers were washed with a sat. aq solution of NaHCO3 (40 mL), dried over anhyd Na2SO4, and concentrated in vacuo. The residual oil was purified by flash chromatography over silica gel (CH2Cl2 → MeOH-CH2Cl2, 1:9) to first give regioisomers 5a-g and then the corresponding diastereo- and enantiomerically pure acetylenic α-amino alcohols 4a-g.