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
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
收藏
页码:1021 / 1028
页数:8
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