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Volumn 38, Issue 6, 1997, Pages 927-930

An in situ procedure for catalytic, enantioselective acetate aldol addition. Application to the synthesis of (R)-(-)-epinephrine

Author keywords

[No Author keywords available]

Indexed keywords

ADRENALIN;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0031562040 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(96)02515-4 Document Type: Article

Times cited : (47)

References (17)

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- and references therein
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- iPrO)4 (0.020 equiv). The orange solution was stirred for 1 h at 23 °C prior to adding via cannula a 10 mM toluene solution of 3,5-di-tert-butylsalicylic acid (0.040 equiv, dried by dissolving in toluene and concentrating in vacuo twice). Stirring was continued for an additional hour at 23 °C and then the solution was cooled to -20 °C. To the cooled solution was added trimethylsilyl chloride (0.20 equiv) followed by triethylamine (1.0 equiv) and the aldehyde (1.0 equiv). After stirring the resulting solution for 15 min, the silyl ketene acetal (2.0 equiv) was added dropwise neat. The reaction was allowed to gradually warm to 23 °C over 6 h before it was quenched by pouring onto water.
- 4 and concentrated in vacuo. Purification by chromatography on silica gel gave the β-hydroxy ester adduct.

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