NOVEL RING-CLEAVAGE BASED ON INTERMOLECULAR ALDOL CONDENSATION

被引：22

作者：

NAGUMO, S ^{[1
]}

MATSUKUMA, A ^{[1
]}

SUEMUNE, H ^{[1
]}

SAKAI, K ^{[1
]}

机构：

[1] KYUSHU UNIV,FAC PHARMACEUT SCI,FUKUOKA 812,JAPAN

来源：

TETRAHEDRON | 1993年 / 49卷 / 46期

关键词：

RING CLEAVAGE; INTERMOLECULAR ALDOL CONDENSATION; GROB FRAGMENTATION; BORON TRIFLUORIDE ETHERATE (R,R)-3,5-DIMETHYLCYCLOHEXANONE; ETHYLENE GLYCOL;

D O I：

10.1016/S0040-4020(01)81545-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 crossed intermolecular aldol condensation was also examined, and the reaction pathway was discussed.

引用

页码：10501 / 10510

页数：10

共 9 条

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