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Synlett 1990; 1990(12): 763-765
DOI: 10.1055/s-1990-21244
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Diastereoselective Ring Opening of 2-Substituted N-Benzyl-4,4, 7α-trimethyl-trans-octahydro-1,3-benzoxazines by Grignard Reagents. Highly Enantioselective Synthesis of Primary Amines

Angel Alberola* , Celia Andrés, Rafael Pedrosa
  • *Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, Dr. Mergelina s/n., E-47011 Valladolid, Spain
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Publikationsdatum:
08. März 2002 (online)

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2-Alkyl-N-benzyl-4,4,7α-trimethyl-trans-octahydro-1,3-benzoxazines, prepared from [1R(1α,2β,5α)]-5-methyl-2-(1-benzylamino-1-methylethyl)cyclohexanol and aldehydes, react with Grignard reagents with high diastereoselectivity. The sequential elimination of the chiral auxiliary with phosphorus pentoxide and hydrogenolysis of the benzyl group provides the corresponding primary amines in very good chemical yield and with high enantiomeric excess.