ISSN:
0894-3230
Keywords:
Organic Chemistry
;
Physical Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Physics
Notes:
Cyclopentannulation of 4-tert-butyldimethylsilyloxy-2-cyclopenten-1-one from a β-metallated dioxolane-type orthoester affords 4-tert-butyldimethylsilyloxy-8,8-ethylenedioxy-6-phenylsuiphonyl-2-oxobicyclo [3·3·0] octanes as a mixture of two diastereoisomers. Their stereochemical structures were established by NMR and x-ray analysis. The minor product possesses a cis ring fusion, the sulphonyl and the tert-butyldimethylsilyloxy groups being endo and exo, respectively. The major isomer also has a cis ring fusion but an exo position for both dimethylsilyloxy and sulphonyl groups. Both cyclopentannulation products result from an anti addition with respect to the 4-tert-butyldimethylsilyloxy group on the enone.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/poc.610061009
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