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Substituent Effect on the Asymmetric Induction with (1R,2S,5R)-and (1S,2R,5S)-menthol Auxiliaries

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dc.creator Er, Mustafa
dc.creator Coskun, Necdet
dc.date 2010-03-31T21:00:00Z
dc.date.accessioned 2020-10-06T11:24:23Z
dc.date.available 2020-10-06T11:24:23Z
dc.identifier d0b515b2-de09-47e2-ad88-eb3de20bb2fb
dc.identifier https://avesis.sdu.edu.tr/publication/details/d0b515b2-de09-47e2-ad88-eb3de20bb2fb/oai
dc.identifier.uri http://acikerisim.sdu.edu.tr/xmlui/handle/123456789/72654
dc.description Substituted benzaldehydes reacts in cis-diastereoselective manner with menthyl haloacetates in the presence of phase transfer catalyst and a base in THF at room temperature to, give the corresponding 3-aryloxirane-2-carboxylates (2/3a-h) in moderate to high yields. The magnitude of asymmetric induction in the latter reaction was quantified by a Hammett type equation log(2/3)(X) = p sigma(1) + log(2/3)(X=H). The stereochemistry of compounds 2 and 3 was elucidated by correlation with (4S,5R)-2,4-dipheny1-4,5-dihydrooxazole-5-carboxylic acid (+)-8 as well as its enantiomer (-)-8.
dc.language eng
dc.rights info:eu-repo/semantics/closedAccess
dc.title Substituent Effect on the Asymmetric Induction with (1R,2S,5R)-and (1S,2R,5S)-menthol Auxiliaries
dc.type info:eu-repo/semantics/article

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