Download PDF
Synlett 1997; 1997(8): 974-976
DOI: 10.1055/s-1997-946
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.

A Simple and Highly Diastereoselective One-Pot Synthesis of Mannich-Bases

Michael Arend, Nikolaus Risch*
  • *Fachbereich Chemie und Chemietechnik, Universität-Gesamthochschule Paderborn, Warburger Str. 100, D-33098 Paderborn, Germany, Fax +5251/60-3245; E-mail: nr@chemie.uni-paderborn.de
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

A convenient one-pot procedure for the synthesis of β-amino ketones 5 from economical shelf reagents is described. Iminium salts 3 are generated in virtually quantitative yields from secondary amines 1 and aldehydes 2 mediated by NaI/Me3SiCl/NEt3. Subsequently, the salts 3 are used for the in situ aminoalkylation of enamines 4. The method provides the Mannich bases 5 in high yields and excellent diastereoselectivities (>96 % ds). It can also be applied for the aminoalkylation of other nucleophiles such as imines or electron-rich aromatic compounds.

β-amino ketones - diastereoselective aminoalkylation - enamines - imines - iminium salts