Synthesis of enantiomerically pure ( E)-1,1,3,3,6,6-hexamethyl-1-sila-4-cycloheptene and its absolute configuration

The title compound 1, a highly strained ( E)-cycloalkene, was prepared in enantiomerically pure form from the corresponding trans-1,2-diol 4 via the thionocarbonate 5. The racemic 4 was separated by enantioselective HPLC on an amylose tris(3,5-dimethylphenylcarbamate) column. The absolute configurat...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron: asymmetry 1999-09, Vol.10 (18), p.3483-3492
Main Authors: Krebs, Adolf W, Thölke, Bernd, Pforr, Karl-Ingo, König, Wilfried A, Scharwächter, Klaus, Grimme, Stefan, Vögtle, Fritz, Sobanski, Adam, Schramm, Jörg, Hormes, Josef
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The title compound 1, a highly strained ( E)-cycloalkene, was prepared in enantiomerically pure form from the corresponding trans-1,2-diol 4 via the thionocarbonate 5. The racemic 4 was separated by enantioselective HPLC on an amylose tris(3,5-dimethylphenylcarbamate) column. The absolute configuration of 1 was determined by circular dichroism spectroscopy in connection with theoretical calculations; the (+)-enantiomer has the ( S)- and the (−)-enantiomer the ( R)-configuration.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(99)00313-4