DIASTEREOSELECTIVE SYNTHESIS OF PYRIDYL SUBSTITUTED THIAZOLIDIN-4-ONES - NEW LIGANDS FOR THE CU(I) CATALYZED ASYMMETRIC CONJUGATE ADDITION OF DIETHYLZINC TO ENONES

Authors
DEVRIES AHM HOF RP STAAL D KELLOGG RM FERINGA BL
Citation
Ahm. Devries et al., DIASTEREOSELECTIVE SYNTHESIS OF PYRIDYL SUBSTITUTED THIAZOLIDIN-4-ONES - NEW LIGANDS FOR THE CU(I) CATALYZED ASYMMETRIC CONJUGATE ADDITION OF DIETHYLZINC TO ENONES, Tetrahedron : asymmetry, 8(10), 1997, pp. 1539-1543
Citations number
30
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
1539 - 1543
Database
ISI
SICI code
0957-4166(1997)8:10<1539:DSOPST>2.0.ZU;2-I
Abstract
Several novel thiazolidin-4-ones have been synthesized from chiral non -racemic alpha-mercapto acids by a three component reaction in high yi elds and with diastereomeric excesses up to 91%. After recrystallizati on, the thiazolidinones were obtained diastereomerically pure and were employed as chiral ligands in the copper catalyzed conjugate addition of diethylzinc to cyclohexenone and chalcone as model substrates. Ena ntioselectivities up to 62% were achieved. (C) 1997 Elsevier Science L td.