NEW AXIALLY CHIRAL SULFUR-COMPOUNDS - SYNTHESIS AND CONFORMATIONAL STABILITY OF ENANTIOPURE 4,4'-BIPHENANTHRENE-3,3'-DITHIOL AND RELATED ATROPISOMERIC DERIVATIVES

被引：40

作者：

DORE, A

FABBRI, D

GLADIALI, S

VALLE, G

机构：

[1] UNIV SASSARI,DIPARTIMENTO CHIM,I-07100 SASSARI,ITALY

[2] UNIV PADUA,CTR STUDIO BIOPOLIMERI,I-35131 PADUA,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 03期

关键词：

D O I：

10.1016/0957-4166(95)00074-Y

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantiopure (R)- and (S)-4,4'-biphenanthrene-3,3'-dithiol la has been prepared for the first time through a synthetic procedure involving in the key step a stereoconservative Newman-Kwart thermorearrangement of the bis-N,N-dimethylthiocarbamoyl ester of(R)- and (S)-biphenanthrol 2b, respectively. The atropisomeric conformations of la are not interconverted even at temperatures as high as 285 degrees C, whereas the related biphenanthrothiophene 3 is completely racemized in a few minutes at 250 degrees C. The axially chiral backbone of la has been incorporated in a set of novel C-2 symmetry sulfur reagents suitable for a variety of stereoselective reactions.

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页码：779 / 788

页数：10

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