Premium
The Stereoselective Acylation of Racemic Secondary Alcohols with Phenyltrifluoromethylketene as an Experimental Test of the Stereochemical Analogy Model
Author(s) -
Anders Ernst,
Ruch Ernst,
Ugi Ivar
Publication year - 1973
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.197300251
Subject(s) - stereoselectivity , acylation , diastereomer , analogy , chemistry , stereochemistry , product (mathematics) , organic chemistry , mathematics , catalysis , linguistics , geometry , philosophy
Validity of the stereochemical analogy model [1,2] for stereoselective reactions is tested on acylations of racemic chiral secondary alcohols with phenyltrifluoromethylketene. The product ratios for the diastereomeric esters formed can be calculated using a formula derived from the general model for the special case, the results agreeing with the experimental data within the accuracy of the measuring method (integration of the 19 F‐NMR signals).