Stereoselective Synthesis of Dienic Nitrogen Compounds

Ramzi Aït Youcef; Charlotte Boucheron; Stéphane Guillarme; Stéphanie Legoupy; Didier Dubreuil; François Huet

doi:10.1055/s-2006-926303

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Synthesis 2006(4): 633-636
DOI: 10.1055/s-2006-926303

PAPER

Stereoselective Synthesis of Dienic Nitrogen Compounds

Ramzi Aït Youcef^a, Charlotte Boucheron^a, Stéphane Guillarme^a, Stéphanie Legoupy*^a, Didier Dubreuil^b, François Huet*^a
^a Laboratoire de Synthèse Organique, UCO2M, UMR CNRS 6011, Université du Maine, avenue Olivier Messiaen, 72085 Le Mans cedex 9, France
^b Laboratoire de Synthèse Organique, UMR CNRS 6513, FR CNRS 2465, 2 rue de la Houssinière, BP 92208, 44322 Nantes cedex 03, France
Fax: +33(2)43833902; e-Mail: stephanie.legoupy@univ-lemans.fr; e-Mail: francois.huet@univ-lemans.fr;

Further Information

Publication History

Received 1 July 2005
Publication Date:
19 January 2006 (online)

Abstract
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Abstract

Eight dienic nitrogen compounds were prepared starting from cyclobutene lactam 8. Dienes 12-15 were obtained by benzylation or acylation followed by methanolysis, hydrolysis or reduction. The unsubstituted lactam 8 provided diene 16. The latter was a precursor for the mono and biacylated products 17-19.

Key words

electrocyclic reactions - lactams - ring opening - dienes - torquoselectivity

References

1a Petrzilka M. Grayson JI. Synthesis 1981, 753

Article in Thieme Connect Google Scholar
1b Campbell AL. Lenz GR. Synthesis 1987, 421

Article in Thieme Connect Google Scholar
2a Oppolzer W. Fröstl W. Helv. Chim. Acta 1975, 58: 587

Crossref Google Scholar
2b Oppolzer W. Fröstl W. Helv. Chim. Acta 1975, 58: 590

Crossref Google Scholar
2c Oppolzer W. Fröstl W. Weber HP. Helv. Chim. Acta 1975, 58: 593

Crossref Google Scholar
2d Oppolzer W. Bieber L. Francotte E. Tetrahedron Lett. 1979, 20: 981

Crossref Google Scholar
3a Overman LE. Taylor GF. Jessup PJ. Tetrahedron Lett. 1976, 3089

Crossref Google Scholar
3b Overman LE. Taylor GF. Petty CB. Jessup P. J. Org. Chem. 1978, 43: 2164

Crossref Google Scholar
3c Overman LE. Taylor GF. Houk KN. Domelsmith LN. J. Am. Chem. Soc. 1978, 100: 3182

Crossref Google Scholar
3d Overman LE. Jessup PJ. J. Am. Chem. Soc. 1978, 100: 5179

Crossref Google Scholar
4 Berthon L. Uguen D. Tetrahedron Lett. 1985, 26: 3975

Crossref Google Scholar
5 Kozmin SA. Rawal VH. J. Org. Chem. 1997, 62: 5252

Crossref Google Scholar
6 Tanaka R. Hirano S. Urabe H. Sato F. Org. Lett. 2003, 5: 67

Crossref Google Scholar
7a Behr J.-B. Defoin A. Pires J. Streith J. Macko L. Zehnder M. Tetrahedron 1996, 52: 3283

Crossref Google Scholar
7b Zezza CA. Smith MB. J. Org. Chem. 1988, 53: 1161

Crossref Google Scholar
7c McAlonan H. Murphy JP. Nieuwenhuyzen M. Reynolds K. Sarma PKS. Stevenson PJ. Thompson N. J. Chem. Soc., Perkin Trans. 1 2002, 69

Crossref Google Scholar
8a Barluenga J. Fernandez MA. Aznar F. Valdés C. Chem. Commun. 2004, 1400

Crossref Google Scholar
8b Barluenga J. Rodriguez F. Alvarez-Rodrigo L. Fañanás FJ. Chem. Eur. J. 2004, 10: 101

Crossref Google Scholar
8c Commins DL. Joseph SP. Chen X. Tetrahedron Lett. 1995, 36: 9141

Crossref Google Scholar
9 Niwayama S. Kallel EA. Spelmeyer DC. Sheu C. Houk KN. J. Org. Chem. 1996, 61: 2813

Crossref PubMed Google Scholar
10 Gourdel-Martin M.-E. Huet F. Tetrahedron Lett. 1996, 37: 7745

Crossref Google Scholar
11 Gauvry N. Huet F. J. Org. Chem. 2001, 66: 583

Crossref Google Scholar
12 Jaroszewski JW. Grossen P. Mohr P. Tamm C. Helv. Chim. Acta 1986, 69: 718

Crossref Google Scholar
13 Dilling WL. Org. Photochem. Synth. 1976, 2: 5

Google Scholar