Asymmetric synthesis of 5-and 6-membered lactones from cyclic substrates bearing a C2-chiral auxiliary
Y Yamamoto, A Sakamoto, T Nishioka…
Index: Yamamoto, Yukio; Sakamoto, Akio; Nishioka, Takaaki; Oda, Jun'ichi; Fukazawa, Yoshimasa Journal of Organic Chemistry, 1991 , vol. 56, # 3 p. 1112 - 1119
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Citation Number: 34
Abstract
Optically active lactones were synthesized by a novel asymmetric synthesis in which enantiotopic groups remote from a prochiral center were effectively discriminated. The cyclic, diamide alcohols bearing a C2-chiral auxiliary,(+)-[l, l'-binaphthyl]-2, 2'-diamine (4), were designed and prepared such that the hydroxyl group should attack preferentially at one of the two carbonyl groups. By the catalytic action of trifluoroacetic acid, the substrates 6a, b ...
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