二氯化锡辅助通过半频哪醇重排合成 N-保护的γ-氨基β-酮酯。
Tin(II) chloride assisted synthesis of N-protected γ-amino β-keto esters through semipinacol rearrangement.
机构信息
Department of Chemistry, Indian Institute of Science Education and Research, Garware Circle, Pashan, Pune, 411021, India.
出版信息
Org Biomol Chem. 2010 Nov 7;8(21):4855-60. doi: 10.1039/c0ob00199f. Epub 2010 Aug 24.
PMID:20734011
Abstract
A facile synthetic route for the preparation of N-protected γ-amino β-keto esters from amino aldehydes and ethyl diazoacetate is described. The two component coupling is facilitated by tin(II) chloride followed by semipinacol rearrangement leading to the product in quantitative yield. The reaction is mild, instantaneous and compatible with Boc-, Fmoc- and Cbz-amino protecting groups.
摘要
描述了一种从氨基酸醛和重氮乙酸乙酯制备 N-保护的γ-氨基β-酮酯的简便合成路线。锡(II)氯化物促进了两部分偶联，然后进行半频哪醇重排，以定量产率得到产物。该反应条件温和、瞬时，并且与 Boc、Fmoc 和 Cbz 氨基保护基兼容。
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