(6 S, 7 S, 10 R)-and (6 R, 7 S, 10 R)-7-isopropyl-10-methyl-4-oxo-1, 5-dioxaspiro [5.5] undec-2-enes having an electron-withdrawing substituent at the 2-position: …

M Sato, C Orii, J Sakaki, C Kaneko

Index: Sato, Masayuki; Orii, Chisato; Sakaki, Jun-ichi; Kaneko, Chikara Journal of the Chemical Society, Chemical Communications, 1989 , # 19 p. 1435 - 1436

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Abstract

Chiral spirocyclic dioxinones (S)-(6) and (S)-(7) have been synthesized from (–)-menthone and used in Diels–Alder reactions with cyclopentadiene; remarkable diastereofacial selectivity (isopropyl side) and endo preference observed in these reactions have offered a new methodology for asymmetric Diels–Alder reactions.