Tandem Isomerization-Mannich Reactions from Allylic Alcohols and their Use for the Preparation of Four Diastereoisomers of 1-Amino-2-Methyl-1- Phenyloctan-3-ol

Hai   T.   Cao; Thierry      Roisnel; Rene      Gree

doi:10.2174/157017809789124858

Abstract

The tandem isomerization-Mannich reaction of octen-3-ol and benzylidene N-sulfonyl imine affords the corresponding β-aminoketones in good yields. Diastereoselective reduction, followed by the deprotection of the primary amine, gives the expected 1-amino-2-methyl-1-phenyloctan-3-ol derivatives in excellent yields and in diastereomerically pure forms.

Keywords: Mannich reaction, 1,3 aminoalcohols, allylic alcohols, iron, catalysis

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Letters in Organic Chemistry

Title: Tandem Isomerization-Mannich Reactions from Allylic Alcohols and their Use for the Preparation of Four Diastereoisomers of 1-Amino-2-Methyl-1- Phenyloctan-3-ol

Volume: 6 Issue: 6

Author(s): Hai T. Cao, Thierry Roisnel and Rene Gree

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Keywords: Mannich reaction, 1,3 aminoalcohols, allylic alcohols, iron, catalysis

Abstract: The tandem isomerization-Mannich reaction of octen-3-ol and benzylidene N-sulfonyl imine affords the corresponding β-aminoketones in good yields. Diastereoselective reduction, followed by the deprotection of the primary amine, gives the expected 1-amino-2-methyl-1-phenyloctan-3-ol derivatives in excellent yields and in diastereomerically pure forms.

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Cao T. Hai, Roisnel Thierry and Gree Rene, Tandem Isomerization-Mannich Reactions from Allylic Alcohols and their Use for the Preparation of Four Diastereoisomers of 1-Amino-2-Methyl-1- Phenyloctan-3-ol, Letters in Organic Chemistry 2009; 6 (6) . https://dx.doi.org/10.2174/157017809789124858