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2005
Carboxylic amides
Q 0490
Enantioselective Formal Hydration of α,β-Unsaturated Imides by Al-Catalyzed
Addition of Oxime Nucleophiles. — The first catalytic asymmetric con09- 069 Conjugate
jugate addition of an oxygen-centered nucleophile to α,β-unsaturated imides is presented. The reaction affords oxime ethers in high enantioselectivities, which subsequently
are hydrogenated to release the corresponding β-hydroxy imides (II), (IV), (V), (VII)
and (VIII). Thus, the presented synthesis provides a formal asymmetric hydration of
α,β-unsaturated imides. — (VANDERWAL, C. D.; JACOBSEN*, E. N.; J. Am.
Chem. Soc. 126 (2004) 45, 14724-14725; Dep. Chem. Chem. Biol., Harvard Univ.,
Cambridge, MA 02138, USA; Eng.) — Mischke
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