Copper(I)-Catalyzed IntramolecularAddition of N-Chloroamides to Double Bonds;an Efficient Synthesis of Lactams from Unsaturated Amides

Iris Anne Schulte-Wülwer; Juho Helaja; Richard Göttlich

doi:10.1055/s-2003-40997

PAPER

Copper(I)-Catalyzed IntramolecularAddition of N-Chloroamides to Double Bonds;an Efficient Synthesis of Lactams from Unsaturated Amides

Iris Anne Schulte-Wülwer, Juho Helaja, Richard Göttlich*
Organisch-Chemisches Institut der WestfälischenWilhelms-Universität Münster, Corrensstr.40, 48149 Münster, Germany
e-Mail: gottlir@uni-muenster.de;

Abstract

All articles of this category

Abstract

Copper(I) salts catalyse the intramolecular addition of N-chloramides to carbon-carbondouble bonds leading to lactams in almost quantitative yield.

Key words

catalysis - copper - lactams - radicalreactions

Full Text

References

References:

1a Dalton DR. The Alkaloids MarcelDekker; New York: 1979.

1b Gilchrist TL. Heterocyclenchemie VCH; Weinheim: 1995.

2 Müller TE. Beller M. Chem. Rev. 1998, 98: 675

3a Kuehne ME. Horne DA. J. Org. Chem. 1975, 40: 1278

3b Lessard J. Cote R. Mackiewicz P. Furstoss R. Waegell B. J.Org. Chem. 1978, 43: 3750

4a Göttlich R. Synthesis 2000, 1561

4b Heuger G. Kalsow S. Göttlich R. Eur.J. Org. Chem. 2002, 1848

5a Kochi JK. Free Radicals Wiley; NewYork: 1973.

5b Kochi JK. Acc. Chem. Res. 1974, 7: 351

6 Bowden K. Heilbron I. Jones E. Weedon B. J. Chem. Soc. 1946, 39

7

The NCS used was dried by azeotropicremoval of H₂O with toluene and then recrystallised fromtoluene.

Compounds 5b-f are known, see (4) and:

8a Toshimitsu A. Terao K. Uemura S. J.Org. Chem. 1986, 51: 1724

8b Sennyey G. Barcelo G. Senet J.-P. TetrahedronLett. 1987, 28: 5809

9 Blenderman WG. Joullie MM. Preti G. J.Org. Chem. 1983, 48: 3206

10 Hanko R. Hoppe D. Angew. Chem. 1981, 93: 115

11a Newcomb M. Esker JL. TetrahedronLett. 1991, 32: 1035

11b Clark AJ. Peacock JL. TetrahedronLett. 1998, 39: 6029