Title: ASYMMETRIC SYNTHESIS BASED ON (<i>Z</i>)-(2<i>R</i>,3<i>S</i>)-6-BENZYLIDENE-3,4-DIMETHYL-5,7-DIOXO-2-PHENYLPERHYDRO-1,4-OXAZEPINE. SYNTHESIS OF OPTICALLY ACTIVE 3-SUBSTITUTED 3-PHENYLPROPIONIC ACIDS
Abstract: Abstract (Z)-(2R,3S)-6-Benzylidene-3,4-dimethyl-5,7-dioxo-2-phenylperhydro-1,4-oxazepine (I) was prepared in good yield from α-ethoxycarbonylcinnamic acid and l-ephedrine hydrochloride by the use of 2-chloro-1-methylpyridinium tosylate as a coupling reagent. The conjugate addition of n-butylmagnesium bromide to (I) in the presence of nickel chloride, followed by hydrolysis and decarboxylation gave highly enantiomerically pure (99%) 3-phenylheptanoic acid in high yield (92%).
Publication Year: 1977
Publication Date: 1977-10-01
Language: en
Type: article
Indexed In: ['crossref']
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Cited By Count: 27
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