Kinetic resolution of secondary alcohols. Enantioselective acylation mediated by a chiral (dimethylamino)pyridine derivative

Journal of the American Chemical Society

Volumn 118, Issue 7, 1996, Pages 1809-1810

  Vedejs, Edwin ^a   Chen, Xinhai ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL;

ARTICLE; CHEMICAL REACTION KINETICS; DRUG IDENTIFICATION; DRUG PURIFICATION; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE;

EID: 0029876822     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953631f     Document Type: Article

References (31)

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28. 2 for the specified time (Table 1). and the neutral products were separated by flash chromatography prior to assay
29. 5 Due to the logarithmic nature of the calculation, as little as 5% undetected impurity, side reaction, racemization, or integral error (used to measure percent conversion) could account for the discrepancy in s values. At most, traces (< 1%) of racemization were detected by exposing 6e to zinc chloride + (PMP), or with added 3, or with PMP-HCl added (HPLC assay). Racemization cannot be ruled out, but error in percent conversion is the more likely source of the discrepancy. However, racemization of product ester or the recovered alcohol may explain why marginal results were obtained with the sensitive 1-(2-methoxyphenyl)-ethanol (maximum 15-30% ee for the ester as well as the recovered alcohol).
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