OPTICALLY-ACTIVE AXIALLY CHIRAL ANILIDE AND MALEIMIDE DERIVATIVES AS NEW CHIRAL REAGENTS - SYNTHESIS AND APPLICATION TO ASYMMETRIC DIELS-ALDER REACTION

Citation
O. Kitagawa et al., OPTICALLY-ACTIVE AXIALLY CHIRAL ANILIDE AND MALEIMIDE DERIVATIVES AS NEW CHIRAL REAGENTS - SYNTHESIS AND APPLICATION TO ASYMMETRIC DIELS-ALDER REACTION, Journal of organic chemistry, 63(8), 1998, pp. 2634-2640
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
00223263
Volume
63
Issue
8
Year of publication
1998
Pages
2634 - 2640
Database
ISI
SICI code
0022-3263(1998)63:8<2634:OACAAM>2.0.ZU;2-7
Abstract
New axially chiral N-acryl-N-allyl-o-tert-butylanilide and N-(o-tert-b utylphenyl)-2-methylmaleimide with high optical purity and definite ab solute configurations were prepared from o-tert-butylaniline and (S)-O -acetyl lactic acid or (R)-2-methylsuccinic acid, respectively. Iodine -or Lewis acid-mediated asymmetric Diels-Alder reaction of these axial ly chiral compounds with various dienes proceeded with high endo and d iastereofacial selectivity.