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Asymmetric synthesis of 5-and 6-membered lactones from cyclic substrates bearing a C2-chiral auxiliary

Y Yamamoto, A Sakamoto, T Nishioka…

文献索引: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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被引用次数: 34

摘要

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 ...