(2S,4R)-N-Benzyloxycarbonyl-4-tosyloxyproline methyl ester, readily prepared from commercially available (2S,4R)-N-benzyl-oxycarbonyl-4-hydroxyproline, was converted to (S)-3,4-dehydroproline of high enantiomeric purity by a process which involved a highly regioselective phenylselenoxide elimination to introduce the olefinic function.
Azoxyalkanes were found to be regiospecifically formed in the reactions of some alkyllithium and Grignard reagents with N-nitroso-O,N-dialkylhydroxylamines. Remarkably, although (Z)-stereomers were usually produced, in one case the (E)-isomer was predominant.
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