Research Article

Synthesis of Three-, Five-, and Six-Membered Heterocycles Derived from New β-Amino-α-(trifluoromethyl) Alcohols

  1. Emilia Obijalska1,†,
  2. Grzegorz Mlostoń1,
  3. Anthony Linden2,
  4. Heinz Heimgartner2

Article first published online: 16 SEP 2010

DOI: 10.1002/hlca.201000232

Issue

Helvetica Chimica Acta

Helvetica Chimica Acta

Volume 93, Issue 9, pages 1725–1736, September 2010

Additional Information

How to Cite

Obijalska, E., Mlostoń, G., Linden, A. and Heimgartner, H. (2010), Synthesis of Three-, Five-, and Six-Membered Heterocycles Derived from New β-Amino-α-(trifluoromethyl) Alcohols. HCA, 93: 1725–1736. doi: 10.1002/hlca.201000232

Author Information

  1. 1

    University of Łódź, Department of Organic and Applied Chemistry, Tamka 12, PL-91-403 Łódź, (phone: +48 42 635 5761; fax: +48 42 665 5162)

  2. 2

    Organisch-chemisches Institut der Universität Zürich, Winterthurerstrasse 190, CH-8057 Zürich, (phone: +41 44 635 4282; fax: +41 44 635 6812)

  1. †

    Part of the planned Ph.D. thesis of E. O., University of Łódź.

  1. †

    Part of the planned Ph.D. thesis of E. O., University of Łódź.

Publication History

  1. Issue published online: 16 SEP 2010
  2. Article first published online: 16 SEP 2010
  3. Manuscript Received: 15 JUN 2010

SEARCH

SEARCH BY CITATION

ARTICLE TOOLS

Get PDF (269K)

Keywords:

  • Alcohols, β-amino-α-(trifluoromethyl);
  • Aziridines, 2-(trifluoromethyl)-;
  • 1,3-Oxazolidines, 5-(trifluoromethyl)-;
  • 1,3,2-Oxazaphospholidines, 5-(trifluoromethyl)-;
  • 1,2,3-Oxathiazolidines, 5-(trifluoromethyl)-;
  • Trifluoromethyl heterocycles;
  • X-Ray crystallography

Abstract

Nucleophilic trifluoromethylation of α-imino ketones 2, derived from arylglyoxal, with Ruppert–Prakash reagent (CF3SiMe3) offers a convenient access to the corresponding O-silylated β-imino-α-(trifluoromethyl) alcohols. In a ‘one-pot’ procedure, by treatment with NaBH4, these products smoothly undergo reduction and desilylation yielding the expected β-amino-α-(trifluoromethyl) alcohols 4. The latter were used as starting materials for the synthesis of diverse trifluoromethylated heterocycles, including aziridines 5, 1,3-oxazolidines 8, 1,3-oxazolidin-2-ones 9, 1,3,2-oxazaphospholidine 2-oxides 10, 1,2,3-oxathiazolidine 2-oxides 11, and morpholine-2,3-diones 12. An optically active 5-(trifluoromethyl)-substituted 1,3-oxazolidin-2-one 9g was also obtained.

Get PDF (269K)