ABSOLUTE-CONFIGURATION OF 3-SUBSTITUTED 1-AZABICYCLO[2.2.1]HEPTANES

被引：14

作者：

BOELSTERLI, J

EGGNAUER, U

POMBOVILLAR, E

WEBER, HP

WALKINSHAW, M

GOULD, RO

机构：

[1] SANDOZ PHARMA LTD,PRECLIN RES,CH-4002 BASEL,SWITZERLAND

[2] UNIV EDINBURGH,DEPT CHEM,EDINBURGH EH8 9YL,MIDLOTHIAN,SCOTLAND

来源：

HELVETICA CHIMICA ACTA | 1992年 / 75卷 / 02期

关键词：

D O I：

10.1002/hlca.19920750210

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The 1-azabicyclo[2.2.1]heptan-3-exo-ol (2) was resolved by fractional crystallisation of its hydrogen tartrate salts. The enantiomers (+)- and (-)-2 were oxidised to the ketones (-)-4 and (+)-4, respectively (Scheme). CD spectroscopy suggested that (-)-4 possesses the (1R,4S)-configuration. This absolute configuration was confirmed by single-crystal X-ray diffraction of the derivative (+)-(1R,4R)-3-(1,3-dithian-2-ylidene)-1-azabicyclo[2.2.1]-heptane ((+)-5).

引用

页码：507 / 512

页数：6

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