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Letters in Organic Chemistry


ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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

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

Volume 6, Issue 6, 2009

Page: [507 - 510] Pages: 4

DOI: 10.2174/157017809789124858

Price: $65


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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