Stereochemical Studies. XXXVI. Stereoselective Syntheses of trans- and cis-Cinnamic Acid Esters from the Phenylalanine Derivatives

α-Diazo-β-phenyl-propionic acid esters (II) prepared from the phenylalanine derivatives (I) were readily decomposed by the alkoxide in tetrahydrofuran to give trans-cinnamic acid esters (III) stereoselectively, while the decomposition of II in the presence of boron trifluoride etherate and dicyclohe...

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 23; no. 2; pp. 299 - 303
Main Authors TAKAMURA, NORIO, MIZOGUCHI, TOMISHIGE, YAMADA, SHUNICHI
Format Journal Article
LanguageEnglish
Published Tokyo The Pharmaceutical Society of Japan 1975
Japan Science and Technology Agency
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Summary:α-Diazo-β-phenyl-propionic acid esters (II) prepared from the phenylalanine derivatives (I) were readily decomposed by the alkoxide in tetrahydrofuran to give trans-cinnamic acid esters (III) stereoselectively, while the decomposition of II in the presence of boron trifluoride etherate and dicyclohexylcarbodiimide in methylene chloride afforded ciscinnamic acid esters (IV) as sole reaction products.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.23.299