Journal
TETRAHEDRON
Volume 60, Issue 20, Pages 4513-4525Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2004.01.098
Keywords
nucleophilic catalysis; asymmetric catalysis; atropisomerism; esterification; acylation; sec-alcohols
Categories
Ask authors/readers for more resources
The synthesis, CSP-HPLC resolution, and absolute configuration assignment of a series of 4-dialkylaminopyridine-based atropisorneric biaryls are described. Screening of these enantiomerically pure catalysts, which differ only in the nature of the 4-dialkylamino substituent, for the kinetic resolution of 1-(1-naphthyl)ethanol reveals the importance of this group on the selectivity of catalysis. The di-n-butylamino derivative displays the most favourable catalytic profile. The utility of this catalyst for the kinetic resolution of a selection of sec-alcohols, including a precursor for the synthesis of the antidepressant fluoxetine hydrochloride (Prozac(R)) are reported. The possible role of the dialkylamino group in chirality transfer is discussed. (C) 2004 Elsevier Ltd. All rights reserved.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available