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Synlett 2000; 2000(3): 327-330
DOI: 10.1055/s-2000-6524
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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
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Publikationsdatum:
31. Dezember 2000 (online)

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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