Download PDF
Synlett 2000; 2000(3): 327-330
DOI: 10.1055/s-2000-6524
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Full Conversion in Diastereoselective Aldol Additions using "Naked" Enolates under Catalytic Amount of Phosphazene Base: The Hydroxypinanone as Chiral Auxiliary

Arlette Solladié-Cavallo* , Benedetta Crescenzi
  • *Laboratoire de Stéréochimie Organométallique, ECPM/Université L. Pasteur, 25 rue Becquerel, 67087-Strasbourg cedex 2, France; Tel. 33 3 88 13 69 79; Fax 33 3 88 13 69 49; E-mail: ascava@chimie.u-strasbg.fr
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

It was shown that a `naked' enolate can undergo an aldol addition with full conversion provided that the ΔpKa between the aldol product and the conjugated acid of the base (which provides the necessary proton to the aldol-adduct) is large enough (> 6 units). Under such conditions the base being regenerated can be used in catalytic amounts. When the iminoglycinate is derived from hydroxypinanone, 83% of the threo-isomer having ∼ 98% ee (threonine) was obtained.

phosphazene base - catalytic aldolization - threonine

      >