Asymmetric synthesis of functionalized aza-cyclic amino acids with quaternary stereocenters by a phase-transfer-catalyzed alkylation strategy |
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Authors: | Ooi Takashi Miki Takashi Maruoka Keiji |
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Institution: | Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan. |
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Abstract: | Reaction: see text] Practical asymmetric synthesis of functionalized aza-cyclic alpha-amino acid derivatives possessing quaternary stereocenters has been achieved by the phase-transfer-catalyzed alkylation of 2 or 3 using chiral quaternary ammonium bromide 1 as catalyst. Subsequent reduction and alkylation of the 3-keto carbonyl moiety of 4 proceeded with complete diastereochemical control to afford the corresponding beta-hydroxy aza-cyclic alpha-amino acid derivatives having stereochemically defined consecutive quaternary carbon centers. |
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