Diastereoselective Lewis acid-catalysed [4+2] cycloadditions of 3-alkyl-, 3-aryl- and 3-carboxyl-2H-azirines: A route to aziridine containing azabicyclo[4.1.0]heptanes and azatricyclo[2.2.1.0]nonanes

Tetrahedron

Volumn 58, Issue 30, 2002, Pages 5983-5987

  Ray, Colin A ^a   Risberg, Erik ^a   Somfai, Peter ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

Aziridine; Azirine; Hetero Diels Alder reaction

Indexed keywords

2 METHOXY 4 TRIMETHYLSILYLOXY 6 PHENYL 1 AZABICYCLO[4.1.0]HEPT 3 ENE; 2 METHOXY 6 PHENYL 1 AZABICYCLO[4.1.0]HEPT 3 ENE; 4 (2 PHENYLETHYL) 6 TRIMETHYLSILYLOXY 2 AZATRICYCLO[3.2.2.0]NON 6 ENE; 4 PHENYL 6 TRIMETHYLSILYLOXY 2 AZATRICYCLO[3.2.2.0]NON 6 ENE; ALKADIENE; ALKANE DERIVATIVE; AZIRINE DERIVATIVE; BENZYL 2 AZATRICYCLO[3.2.1.0]OCT 6 ENE 4 CARBOXYLATE; BENZYL 2 METHOXY 4 TRIMETHYLSILYLOXY 1 AZABICYCLO[4.1.0]HEPT 3 ENE 6 CARBOXYLATE; BENZYL 2 TRIMETHYLSILYLOXY 1 AZABICYCLO[4.1.0]HEPT 3 ENE 6 CARBOXYLATE; CARBOXYLIC ACID DERIVATIVE; HEPTANE; LEWIS ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CYCLOADDITION; DIASTEREOISOMER; DIELS ALDER REACTION; MASS SPECTROMETRY; PRIORITY JOURNAL; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE; THIN LAYER CHROMATOGRAPHY;

BETULACEAE;

EID: 0037157802     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00611-7     Document Type: Article

References (13)

1. Boger D.L., Weinreb S.M.W. Hetero Diels-Alder Methodology in Organic Chemistry. 1987;Academic, San Diego.
2. Weinreb S.N. Trost B.M., Fleming I., Comprehensive Organic Synthesis. Vol. 5:1991;401 Pergamon, Oxford.
3. Nair V. Hasner A., The Chemistry of Heterocyclic Compounds: Small Ring Heterocycles Part 1. Vol. 42:1983;215 Wiley, New York.
4. Bhullar P., Gilchrist T.L., Maddocks P. Synthesis. 1997;271.
5. Alves M.J., Gilchrist T.L. Tetrahedron Lett. 39:1998;7579.
6. Alves M.J., Gilchrist T.L. J. Chem. Soc., Perkin Trans. 1. 1998;299.
7. (a) Alves M.J., Bickley J.F., Gilchrist T.L. J. Chem. Soc., Perkin Trans. 1. 1999;1399. For pertinent reviews concerning activated 2H-azirines as dienophiles and the chemistry of these species in general see: (b) Gilchrist T.L. Aldrichimia Acta. 34:2001;51 © Palacios F., Ochoa de Retana A.M., Martinez de Marigorta E., de los Santos J.M. Eur. J. Org. Chem. 2001;2401 (d) Buonora P., Olsen J.-C., Oh T. Tetrahedron. 57:2001;6099.
8. Ray C.A., Risberg E., Somfai P. Tetrahedron Lett. 42:2001;9209.
9. Tanner D. Angew. Chem., Int. Ed. Engl. 33:1994;599-619.
10. (a) Hortmann A.G., Robertson D.A., Gillard B.K. J. Org. Chem. 37:1972;322 (b) Gilchrist T.L., Mendoca R. Synlett. 12:2000;1843.
11. Kobayashi S., Busujima T., Nagayama S. Chem. Eur. J. 6:2000;3491.
12. Auricchio S., Grassi S., Malpezzi L., Sartori A.S., Truscello A.M. Eur. J. Org. Chem. 2001;1183.
13. For general experimental, see: Åhman J., Somfai P. Tetrahedron. 51:1995;9747.