H-1-NMR CORRELATION OF CHIRAL 3-PHENYLBUTANOATES FOR THE DETERMINATION OF ABSOLUTE STEREOCHEMISTRY OF CHIRAL ALCOHOLS

Authors
NADKARNI PJ SAWANT MS TRIVEDI GK
Citation
Pj. Nadkarni et al., H-1-NMR CORRELATION OF CHIRAL 3-PHENYLBUTANOATES FOR THE DETERMINATION OF ABSOLUTE STEREOCHEMISTRY OF CHIRAL ALCOHOLS, Tetrahedron : asymmetry, 6(8), 1995, pp. 2001-2010
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
6
Issue
8
Year of publication
1995
Pages
2001 - 2010
Database
ISI
SICI code
0957-4166(1995)6:8<2001:HCOC3F>2.0.ZU;2-5
Abstract
A study of diastereoselective 1,4-addition of phenyl Grignard has been attempted on some chiral crotonates. The Pi-facial selectivities in t hese reactions have been determined on the basis of specific rotations of the hydrolysis product, namely 3-phenyl butanoic acid (3PBA). Corr elation of these results with the results obtained from (1)HNMR shield ings arising due to phenyl anisotropy, has led to conformational corre lation model for the determination of absolute stereochemistry of chir al alcohols.