FUNCTIONALIZED DIORGANOZINC COMPOUNDS - KEY REAGENTS FOR THE SYNTHESIS OF ENANTIOMERICALLY PURE 2,5-DISUBSTITUTED CIS-TETRAHYDROFURANS AND TRANS-TETRAHYDROFURANS

被引：23

作者：

BERNINGER, J ^{[1
]}

KOERT, U ^{[1
]}

EISENBERGHOHL, C ^{[1
]}

KNOCHEL, P ^{[1
]}

机构：

[1] UNIV MARBURG,FACHBEREICH CHEM,D-35032 MARBURG,GERMANY

来源：

CHEMISCHE BERICHTE | 1995年 / 128卷 / 10期

关键词：

SYNTHESIS; STEREOSELECTIVE; CATALYSIS; TETRAHYDROFURANS; DIALKYLZINC REAGENTS;

D O I：

10.1002/cber.19951281010

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

1,4-Diol derivatives 4a-i were synthesized stereoselectively by either reagent- or catalyst-controlled routes using the addition of functionalized diorganozine reagents to aldehydes. The stereoselectivities along the reagent-controlled synthetic path were in the range between 80:20 and 95:5. The stereo-selectivities along the catalyst route exceeded 95:5. The 1,4-diol derivatives 4 thus obtained were transformed into enantiomerically pure cis- and trans-2,5-disubstituted tetrahydrofurans (16-20) by means of an intramolecular Williamson reaction.

引用

页码：1021 / 1028

页数：8

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