Use of Enantiopure Alkoxyallenes in the Enantioselective Preparation  of α-(Alkoxyalkyl)vinyl Ketones

Patrick Rochet; Jean-Michel Vatèle; Jacques Goré

doi:10.1055/s-1993-22363

Synlett 1993; 1993(2): 105-107
DOI: 10.1055/s-1993-22363

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Use of Enantiopure Alkoxyallenes in the Enantioselective Preparation of α-(Alkoxyalkyl)vinyl Ketones

Patrick Rochet^* , Jean-Michel Vatèle, Jacques Goré

^*Laboratoire de Chimie Organique 1, associé au CNRS, Université Claude Bernard Lyon 1, ESCIL - 43 Bd. du 11 Novembre 1918, F-69622 Villeurbanne, France

Abstract

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Homochiral alkoxyallenes, easily prepared from propargylic bromide and a chiral alcohol (aminoalcohols or sugars) are transformed after deprotonation and reaction with an aldehyde to α-hydroxyallenic ethers. The diastereoselection, which largely depends on the chiral auxiliary and on the steric hindrance of the aldehyde is often in the range 50-85%. The acidic hydrolysis of these compounds happens without noticeable racemization providing chiral alcohols 1 with satisfactory enantiomeric excess.

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