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2004
Enantioselective syntheses
O 0031
Double Stereodifferentiation in the "Acetate-Type" Aldol Reaction with Garner's
Stereocontrolled Synthesis of Polyhydroxylated γ-Amino Carbonyl
52- 027 Aldehyde.
Compounds. — The amino alcohol pseudoephedrine is shown to be an excellent auxiliary for the asymmetric acetate reaction with chiral aldehyde (II) under double stereodifferentiation conditions. (R,R)-(-)-(I) and (II) constitute the corresponding matched
combination of reagents, furnishing the aldol adducts in excellent yield and diastereoselectivity. The latter are successfully transformed into chiral building blocks such as
γ-amino- β,δ-dihydroxy acids, esters, and ketones. The auxiliary can be easily recovered after standard acid-base work-up allowing the recycling for further use. —
(VICARIO, J. L.; RODRIGUEZ, M.; BADIA*, D.; CARRILLO, L.; REYES, E.;
Org. Lett. 6 (2004) 18, 3171-3174; Dep. Quim. Org., Fac. Cienc., Univ. Pais Vasco,
E-48080 Bilbao, Spain; Eng.) — Steudel
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