ENANTIOSELECTIVE CONSTRUCTION OF QUATERNARY STEREOGENIC CENTERS POSSESSING A FLUORINE ATOM

被引：31

作者：

IHARA, M ^{[1
]}

TANIGUCHI, N ^{[1
]}

KAI, T ^{[1
]}

SATOH, K ^{[1
]}

FUKUMOTO, K ^{[1
]}

机构：

[1] TOHOKU UNIV,INST PHARMACEUT,SENDAI,MIYAGI 980,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 02期

关键词：

D O I：

10.1039/p19920000221

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Fluorination of methyl (1R,3R,4S)-8-phenylmenthyl methylmalonates 2 using lithium hexamethyl-disilazide and 1-fluoro-2,4,6-trimethylpyridinium triflate (trifluoromethanesulfonate), gave the (R)-3 and (S)- 4 isomers in a 3.8:1 ratio, while fluorination of ethyl-, propyl- and benzyl-malonates 10, 11 and 12 provided the (R)- 13, 15 and 17 and (S)- 14, 16 and 18 isomers in a 1:1.6-2.0 ratio. On the other hand, alkylation of (1R,3R,4S)-8-phenylmenthyl hydrogen fluoromalonates 26 in the presence of lithium hexamethyldisilazide, followed by esterification with diazomethane, produced the (R)- 3, 13, 15, 17-and 27 and (S)- 4, 14, 16, 18 and 28 isomers in a 1:5.7-35 ratio.

引用

页码：221 / 227

页数：7

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