SYNTHESIS AND STEREOCHEMICAL CHARACTERIZATION OF SOME OPTICALLY-ACTIVE 1,2-DINAPHTHYLETHANE-1,2-DIOLS

被引：40

作者：

ROSINI, C ^{[1
]}

SCAMUZZI, S ^{[1
]}

UCCELLOBARRETTA, G ^{[1
]}

SALVADORI, P ^{[1
]}

机构：

[1] CNR,CTR MACROMOLEC STEREORDINATE & OTTICAMENTE ATT,DIPARTIMENTO CHIM & CHIM IND,I-56126 PISA,ITALY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 24期

关键词：

D O I：

10.1021/jo00103a035

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three new diols, 1,2-di(2-naphthyl)ethane-1,2-diol, 1-(1-naphthyl)-2-(2-naphthyl)ethane-1,2-diol, and 1,2-di(1-naphthyl)ethane-1,2-diol, have been prepared in optically active form by catalytic asymmetric syn-dihydroxylation of the corresponding (E)-olefins. The complete stereochemical characterization was easily accomplished by transforming them into the corresponding isopropylidene ketals. These derivatives can be separated by HPLC on a Chiralcel OD column allowing the determination of the ee, and at same time, their CD spectra have been analyzed, allowing a safe assignment of absolute configuration in conjunction with molecular mechanics calculations and an exciton-coupling treatment.

引用

页码：7395 / 7400

页数：6

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