Tetrahedron

Novel ring cleavage based on intermolecular aldol condensation

S Nagumo, A Matsukuma, H Suemune, K Sakai

Index: Nagumo, Shinji; Matsukuma, Aki; Suemune, Hiroshi; Sakai, Kiyoshi Tetrahedron, 1993 , vol. 49, # 46 p. 10501 - 10510

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Citation Number: 14

Abstract

Ring cleavage and reconstruction via intramolecular aldol condensation followed by Grob fragmentation under acetalization conditions (BF3/ethylene glycol) was developed into a novel ring cleavage based on intermolecular aldol condensation. On the basis of this reaction,(R, R)-3, 5-dimethylcyclohexanone was converted into the chiral straight-chain compound with syndiotactic methyl function. The ring cleavage reaction based on a ...