Stereoselective synthesis of azetidine-derived glutamate and aspartate analogues from chiral azetidin-3-ones |
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Authors: | Antonio Carlos B Burtoloso |
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Institution: | a Instituto de Química de São Carlos, Universidade de São Paulo, CP 780, CEP 13566-970, São Carlos, São Paulo, Brazil b Instituto de Química, Universidade Estadual de Campinas, UNICAMP, CP 6154, CEP 13083-970, Campinas, São Paulo, Brazil |
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Abstract: | The stereoselective syntheses of cis conformationally constrained glutamate and aspartate analogues, containing an azetidine framework were accomplished from (S)-N-tosyl-2-phenylglycine in moderate overall yields. The key steps in these syntheses involved an efficient Wittig olefination of an azetidin-3-one, followed by a highly stereoselective rhodium catalyzed hydrogenation. The route could also be applied to the synthesis of a trans glutamate analogue, since epimerization of cis to trans isomer could be performed using DBU in toluene at reflux. |
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