4.8 Article

One-Pot Stereoselective Synthesis of 1,2-Amino Alcohol Derivatives

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ORGANIC LETTERS
卷 13, 期 13, 页码 3426-3429

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AMER CHEMICAL SOC
DOI: 10.1021/ol201173a

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  1. Plan Nacional de Investigacion Cientifica, Desarrollo e Innovacion Tecnologica, Ministerio de Ciencia e Innovacion, Spain [CTQ2009-07109]
  2. FEDER
  3. CSIC

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Common beta-hydroxy amino acids (such as threonine) can be readily transformed into 1,2-amino alcohols with excellent stereoselectivity. This one-pot decarboxylation-alkylation process allows the replacement of the carboxyl group by alkyl, allyl, or aryl groups, generally in high yields. A variation of the process (decarboxylation-Diels-Alder) allows the formation of bi- and polycyclic systems, which are useful precursors of alkaloid cores or iminosugars.

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