Diastereospecific epoxidation/AE kinetic resolution of cis/trans-2,6-dimethylbenzylidene cyclohexane and solution conformation of 4,8-dimethyl-2-phenyl-1-oxaspiro[2.5]octane

John M. Gardiner, Marck Nørret, Ian H. Sadler

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Epoxidation using a (salen)Mn catalyst shows complete selectivity between 2,6-trans and 2,6-cis dimethylbenzylidene cyclohexanes, is diastereospecific, and exhibits a kinetic resolution with k(rel)=5. Stereochemistry and conformation of the product 4,8-dimethyl-2-phenyl-1-oxaspiro[2.5]octane were determined by DQF-COSY and nOe difference measurements at 600MHz.

Original languageEnglish
Pages (from-to)8447-8450
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number46
DOIs
Publication statusPublished - 11 Nov 1996
Externally publishedYes

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