Download PDF
Synlett 1990; 1990(12): 763-765
DOI: 10.1055/s-1990-21244
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
08 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

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.

      >