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