Synlett 2006(16): 2613-2616  
DOI: 10.1055/s-2006-951478
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Diastereoenriched Acetylenic α-N-tert-Butanesulfinamidoalkyl Methoxymethyl Ethers

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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Publikationsverlauf

Received 23 June 2006
Publikationsdatum:
22. September 2006 (online)

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Abstract

The reaction of racemic 3-alkoxy allenylzinc species (±)-1, derived from (methoxymethyl)[(3-trimethylsilyl)prop-2-ynyl]ether (2), with enantiopure (S S)-N-tert-butanesulfinimines 3 leads to the corresponding diastereomerically enriched acetylenic (S S,3S,4R)-α-N-tert-butanesulfinamidoalkyl methoxymethyl ethers 4 with an excellent stereoselectivity.