cheminform abstract: regioselective and stereoselective glycidic oxirane ring opening: a new entry...

2000 oxirane derivatives oxirane derivatives R 0030 40 - 094 Regioselective and Stereoselective Glycidic Oxirane Ring Opening: A New Entry to Optically Pure α-Alkyl α-Hydroxy β-Amino Acid Derivatives. — Chiral oxiranes (I) undergo a BF 3 -catalyzed ring opening with acetonitrile to give oxazolines (III) completely regio- and stereoselectively. However, the 2-phenyl derivatives (V) exhibit complete reversal of the regiose- lectivity but the stereoselectively is lost. Hydrolysis of the oxazolines [cf. (III)] yields β-amino-α-hydroxy carboxylic acid derivatives. — (GARCIA RUANO, JOSE L.; GARCIA PAREDES, CRISTINA; Tetrahedron Lett. 41 (2000) 28, 5357-5361; Dep. Quim. Org., Fac. Cienc., Univ. Auton., Cantoblanco, E-28049 Madrid, Spain; EN) 1

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Page 1: ChemInform Abstract: Regioselective and Stereoselective Glycidic Oxirane Ring Opening: A New Entry to Optically Pure α-Alkyl α-Hydroxy β-Amino Acid Derivatives

2000 oxirane derivatives

oxirane derivativesR 0030

40 - 094Regioselective and Stereoselective Glycidic Oxirane Ring Opening:A New Entry to Optically Pure α-Alkyl α-Hydroxy β-Amino AcidDerivatives. — Chiral oxiranes (I) undergo a BF3-catalyzed ring openingwith acetonitrile to give oxazolines (III) completely regio- and stereoselectively.However, the 2-phenyl derivatives (V) exhibit complete reversal of the regiose-lectivity but the stereoselectively is lost. Hydrolysis of the oxazolines [cf. (III)]yields β-amino-α-hydroxy carboxylic acid derivatives. — (GARCIA RUANO,JOSE L.; GARCIA PAREDES, CRISTINA; Tetrahedron Lett. 41 (2000) 28,5357-5361; Dep. Quim. Org., Fac. Cienc., Univ. Auton., Cantoblanco, E-28049Madrid, Spain; EN)

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NASÝTENÉ KYSLÍKATÉ A SÍRNE HETEROCYKLICKÉ ZLÚČENINYszolcsanyi/education/files/Chemia heterocyklickych zlucenin...Saturated O-heterocycles –Oxirane Structure & Properties