Wittig Reaction with N-Protected 3-(Triphenylphosphonio)alaninates : Synthesis of Optically Active (E)-(2-Arylvinyl)glycine Derivatives
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- ITAYA T.
- Faculty of Pharmaceutical Sciences, Kanazawa University
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- IIDA Takehiko
- Faculty of Pharmaceutical Sciences, Kanazawa University
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- SHIMIZU Shigeyuki
- Faculty of Pharmaceutical Sciences, Kanazawa University
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- MIZUTANI Akemi
- Faculty of Pharmaceutical Sciences, Kanazawa University
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- MORISUE Masatoshi
- Faculty of Pharmaceutical Sciences, Kanazawa University
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- SUGIMOTO Yasushi
- Faculty of Pharmaceutical Sciences, Kanazawa University
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- TACHINAKA Michiko
- Faculty of Pharmaceutical Sciences, Kanazawa University
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Description
(R)-[2-Carboxy-2-[(methoxycarbonyl)amino]ethyl]triphenylphosphonium chloride (1) was converted by treatment with anion exchange resin (HCO^-_3) into the inner salt 13h, which gave a better yield (43%) than 1 in the Wittig reaction with benzaldehyde to afford the [S-(E)]-(2-phenylvinyl)glycine derivative 24. The inner salt 13i bearing an N-benzyloxycarbonyl group was prepared by hydrogenolysis of (R)-[3-benzyloxy-2-[(benzyloxycarbonyl)amino]-3-oxopropyl]triphenylphosphonium chloride (11e) over palladium on carbon, followed by dehydrochlorination. Hydrogenolysis of 11e over Pearlman's catalyst afforded the unprotected phosphonium chloride 12 (X=Cl). N-tert-Butoxycarbonylation of 12 followed by dehydrochlorination afforded 13j, which was more efficiently prepared through hydrogenolysis of (R)-[3-benzyloxy-2-[(tert-butoxycarbonyl)amino]-3-oxopropyl]triphenylphosphonium chloride (11f).The usefulness of 13h-j as building blocks for the synthesis of configurationally labile (2-arylvinyl)glycine derivatives was exemplified by the Wittig reactions with piperonal, which exclusively afforded the (E)-isomers 18h-j with high optical purity in 28-39% yield.
Journal
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- Chem. Pharm. Bull.
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Chem. Pharm. Bull. 41 252-261, 1993
The Pharmaceutical Society of Japan
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Details 詳細情報について
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- CRID
- 1570572702395738752
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- NII Article ID
- 110003630384
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- NII Book ID
- AA00602100
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- ISSN
- 00092363
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- Text Lang
- en
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- Data Source
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- CiNii Articles