CONVERGENT SYNTHESIS OF OPTICALLY-ACTIVE BIFUNCTIONALIZED [7]THIAHETEROHELICENE

被引：23

作者：

TANAKA, K ^{[1
]}

OSUGA, H ^{[1
]}

SHOGASE, Y ^{[1
]}

SUZUKI, H ^{[1
]}

机构：

[1] KYOTO UNIV,FAC SCI,DEPT CHEM,KYOTO 60601,JAPAN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 06期

关键词：

D O I：

10.1016/0040-4039(94)02371-H

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically active bifunctionalized [7]thiaheterohelicene was synthesized using (1R, 2R, 3S, 4S)-endo-3-amino-endo-2-hydroxybornane as a chiral element; The photocyclo-dehydrogenation of 1,2-diarylethylene prepared from benzodithiophenecarboxaldehyde 4 and optically active phosphonium salt 8 gave a 38:62 mixture of the chromatographically separable diastereomers of [7]thiaheterohelicene. The removal of the chiral auxiliary from the diastereomers was readily achieved by thiolysis, and subsequent desilylation and reduction gave new helical ligands possessing C-2 symmetry, (P)- and (M)-2,13-bis(hydroxymethyl)dithieno[3,2-e:3',2'-e']benzo[1,2-b:4,3-b']bis[1]benzothiophenes.

引用

页码：915 / 918

页数：4

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