Enantioselective protonation of samarium enolates derived from α-heterosubstituted ketones and lactone by SmI 2-mediated reduction

Y Nakamura, S Takeuchi, Y Ohgo, M Yamaoka…

Index: Nakamura, Yutaka; Takeuchi, Seiji; Ohgo, Yoshiaki; Yamaoka, Makoto; Yoshida, Akihiro; Mikami, Koichi Tetrahedron, 1999 , vol. 55, # 15 p. 4595 - 4620

Full Text: HTML

Citation Number: 50

Abstract

SmI2-mediated reductive cleavage of α-hetero substituents of α-alkyl or α-aryl ketones and lactone gave the corresponding “thermodynamic samarium enolates”. Enantioselective protonation of the samarium enolates with C2-symmetric chiral diols afforded the corresponding ketones and lactone in moderate to high enantioselectivities.