Ethyl 2-(Diisopropoxyphosphoryl)-2H-azirine-3-carboxylate: Reactions with Nucleophilic
1,3-Dienes

M. José Alves; Américo Lemos; José Enrique Rodriguez-Borges; Xerardo García-Mera; A. Gil Fortes

doi:10.1055/s-0029-1216945

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Synthesis 2009(19): 3263-3266
DOI: 10.1055/s-0029-1216945

PAPER

Ethyl 2-(Diisopropoxyphosphoryl)-2H-azirine-3-carboxylate: Reactions with Nucleophilic 1,3-Dienes

M. José Alves*^a, Américo Lemos*^b, José Enrique Rodriguez-Borges^c, Xerardo García-Mera^d, A. Gil Fortes^a
^a Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal
Fax: +351(253)678983; e-Mail: mja@quimica.uminho.pt;
^b Departamento de Química, Bioquímica e Farmácia, Universidade do Algarve, Campus de Gambelas, 8005-137 Faro, Portugal
Fax: +351(289)819403; e-Mail: alemos@ualg.pt;
^c CIQ, Departamento de Química, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, Portugal
^d Departamento de Química Orgánica, Facultade de Farmacia, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain

Weitere Informationen

Publikationsverlauf

Received 24 March 2009
Publikationsdatum:
21. August 2009 (online)

Abstract
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Abstract

Ethyl 2-(diisopropoxyphosphoryl)-2H-azirine-3-carboxylate, the first example of an azirine bearing simultaneously ester and phosphonate groups was generated in situ and reacted with a number of 1,3-dienes. Cycloadducts or their ensuing rearranged products were isolated in moderate yields.

Key words

2H-azirines - aza-Diels-Alder cycloaddition - dienophiles - phosphonates

References

For reviews, see:
1a Palacios F. Ochoa de Retana AM. Marigorta EM. de los Santos JM. Org. Prep. Proced. Int. 2002, 34: 219

Suche in Google Scholar
1b Gilchrist TL. Aldrichimica Acta 2001, 34: 51

Suche in Google Scholar
1c Palacios F. Ochoa de Retana AM. Marigorta EM. de los Santos JM. Eur. J. Org. Chem. 2001, 2401
2a Pinho e Melo TMVD. Lopes CSJ. Gonçalves AMAR. Beja JA. Paixão AM. Silva MR. Alte da Veiga L. J. Org. Chem. 2002, 67: 66

Suche in Google Scholar
2b Davis FA. Liang C. Liu H. J. Org. Chem. 1997, 62: 3796

Suche in Google Scholar
2c Banert K. Kohler F. Angew. Chem. Int. Ed. 2001, 40: 174

Suche in Google Scholar
3 Heimgartner H. Angew. Chem., Int. Ed. Engl. 1991, 30: 238

Crossref Suche in Google Scholar
4 Miller TW. Tristram EW. Wolf FJ. J. Antibiot. 1971, 24: 48

Crossref Suche in Google Scholar
5 Molinski TF. Ireland CM. J. Org. Chem. 1988, 53: 2103

Crossref Suche in Google Scholar
6a Tanner D. Angew. Chem., Int. Ed. Engl. 1994, 33: 599

Suche in Google Scholar
6b Filigheddu SN. Taddei M. Tetrahedron Lett. 1998, 39: 3857

Suche in Google Scholar
6c Zwanenburg B. Thi LJ. Pure Appl. Chem. 1996, 68: 735

Suche in Google Scholar
6d Davis FA. Liu H. Reddy CV. Tetrahedron Lett. 1996, 37: 5473

Suche in Google Scholar
7a Righi G. D’Achielle R. Tetrahedron Lett. 1996, 37: 6893

Suche in Google Scholar
7b Lim Y. Lee WK. Tetrahedron Lett. 1995, 36: 8431

Suche in Google Scholar
7c Tanner D. Bergsson C. Dhaliwal HK. Tetrahedron Lett. 1990, 31: 1903

Suche in Google Scholar
8 Alves MJ. Gilchrist TL. J. Chem. Soc., Perkin Trans. 1 1998, 299

Crossref
9a Davis FA. Wu Y. Yan H. Prasad KR. McCoull W. Org. Lett. 2002, 4: 655

Suche in Google Scholar
9b Bickley JF. Gilchrist TL. Mendonça R. ARKIVOC 2002, (vi): 192

Suche in Google Scholar
10 Alves MJ. Gil Fortes A. Lemos A. Martins C. Synthesis 2005, 555

Thieme Connect
11a Nair VJ. J. Org. Chem. 1972, 37: 2508

Suche in Google Scholar
11b Hassner A. Anderson DJ. J. Org. Chem. 1974, 39: 2031

Suche in Google Scholar
11c Ray CA. Risberg E. Somfai P. Tetrahedron Lett. 2001, 42: 9289

Suche in Google Scholar
11d Ray CA. Risberg E. Somfai P. Tetrahedron 2002, 58: 5983

Suche in Google Scholar
12a Young AB. Greenamyre JT. Hollingsworth Z. Albin R. D’Amato C. Shoulson I. Penny JB. Science 1988, 241: 981

Suche in Google Scholar
12b Reyes-Rangel G. Marañón V. Avila-Ortiz CG. Parrodi CA. Quintero L. Juaristi E. Tetrahedron 2006, 62: 8404

Suche in Google Scholar
13a Engel R. In Handbook of Organophosphorus Chemistry Dekker Inc.; New York: 1992.
13b Kafarski P. Lejczak B. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 63: 193

Suche in Google Scholar
14a Gilchrist TL. Roberts TG. J. Chem. Soc., Perkin Trans. 1 1983, 1283
14b Ottenheijm HCJ. Plate R. Noordik JH. Herscheid JDM. J. Org. Chem. 1982, 47: 2147

Suche in Google Scholar
15a Palacios F. Ochoa de Retana AM. Gil JI. Ezpeleta JM. J. Org. Chem. 2000, 65: 3213

Suche in Google Scholar
15b Palacios F. Ochoa de Retana AM. Gil JI. Tetrahedron Lett. 2000, 41: 5363

Suche in Google Scholar
15c Palacios F. Ochoa de Retana AM. Gil JI. López de Munain R. Org. Lett. 2002, 4: 2405

Suche in Google Scholar
15d Palacios F. Ochoa de Retana AM. Gil JI. Alonso JM. Tetrahedron: Asymmetry 2002, 13: 2525

Suche in Google Scholar
15e Palacios F. Aparicio D. Ochoa de Retana AM. de los Santos JM. Gil JI. López de Munain R. Tetrahedron: Asymmetry 2003, 14: 689

Suche in Google Scholar
15f Palacios F. Ochoa de Retana AM. Gil JI. Alonso JM. Tetrahedron 2004, 60: 8937

Suche in Google Scholar
16 Alves MJ. Gil Fortes A. Costa FT. Duarte VCM. Tetrahedron 2007, 63: 11167

Crossref Suche in Google Scholar