HIGHLY STEREOSELECTIVE ADDITIONS OF CUPRATES TO A POLYFUNCTIONAL ENONE

Authors
AMIGONI S SCHULZ J MARTIN L LEFLOCH Y
Citation
S. Amigoni et al., HIGHLY STEREOSELECTIVE ADDITIONS OF CUPRATES TO A POLYFUNCTIONAL ENONE, Tetrahedron : asymmetry, 8(10), 1997, pp. 1515-1518
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
10
Year of publication
1997
Pages
1515 - 1518
Database
ISI
SICI code
0957-4166(1997)8:10<1515:HSAOCT>2.0.ZU;2-K
Abstract
The stereoselectivity of the addition of cuprates to a polyfunctional gamma-alkoxy enone depended on the gamma-hydroxyl protective group. Pr otection as a blocking silyl ether gave the best results (de=93-95%). An unexpected and original cleavage-oxidation reaction at ambient temp erature transformed the addition products into well known lactones wel l characterized in the literature. Comparison of the spectral data of these lactones with those in the literature allowed the configuration of the new asymmetric centers to be assigned. (C) 1997 Elsevier Scienc e Ltd.