Diels-Alder reactions of phenylglycinol-derived bicyclic lactams. Enantiodivergent synthesis of cis-hydroisoquinolines

Tetrahedron Asymmetry

Volumn 14, Issue 14, 2003, Pages 2033-2039

  Casamitjana, Núria ^a   Amat, Mercedes ^a   Llor, Núria ^a   Carreras, Marçal ^a   Pujol, Xavier ^a   Fernández, M Montserrat ^a   López, Virgina ^a   Molins, Elies ^b   Miravitlles, Carles ^b   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 (TERT BUTOXYCARBONYL) 8A (HYDROXYMETHYL) 6,7 DIMETHYL 3,4,4A,5,8,8A HEXAHYDRO 1H ISOQUINOLINE; 2 (TERT BUTOXYCARBONYL) 8A (HYDROXYMETHYL) 6,7 DIMETHYL 3,4,4A,8,8A HEXAHYDRO 1H ISOQUINOLINE; 5 OXO 3 PHENYL 6,6 BIS(PHENYLSULFANYL) 2,3,6,7,8,8A HEXAHYDRO 5H OXAZOLO[3.2A]PYRIDINE; 5A BENZENESULFONYL 7,8 DIMETHYL 5 OXO 3 PHENYL 2,3,9,9A,10,10A HEXAHYDRO 6H OXAZOL[3.2B]ISOQUINOLINE; 5A METHOXYCARBONYL 5,8 DIOXO 3 PHENYL 2,39,9A,10,10A HEXAHYDRO 8H OXAZOL[3.2B]ISOQUINOLINE; 5A METHOXYCARBONYL 7,8 DIMETHYL 5 OXO 3 PHENYL 2,3,9,9A,10,10A HEXAHYDRO 6H OXAZOL[3.2B]ISOQUINOLINE; 5A METHOXYCARBONYL 8 METHYL 5 OXO 3 PHENYL 2,3,9,9A,10,10A HEXAHYDRO 6H OXAZOL[3.2B]ISOQUINOLINE; 6 METHOXY 5A METHOXYCARBONYL 5,8 DIOXO 3 PHENYL 2,3,6,7,9,9A,10,10A OCTAHYDRO 8H OXAZOL[3.2B]ISOQUINOLINE; 6 METHOXY 6A METHOXYCARBONYL 5 OXO 3 PHENYL 8 TRIISOPROPYLSILYLOXY 2,3,9,9A,10,10A HEXAHYDRO 6H OXAZOL[3.2B]ISOQUINOLINE; 8A HYDROXYMETHYL 2 (2 HYDROXY 1 PHENYLETHYL) 6,7 DIMETHYL 2,3,4,4A HEXAHYDRO 1H ISOQUINOLINE; 8A HYDROXYMETHYL 2 (2 HYDROXY 1 PHENYLETHYL) 6,7 DIMETHYL 2,3,4,4A,5,8 HEXAHYDRO 1H ISOQUINOLINE; ALKADIENE; GLYCINE DERIVATIVE; ISOQUINOLINE DERIVATIVE; LACTAM; PHENYLGLYCINE; PYRIDINE DERIVATIVE; PYRIDONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CIS ISOMER; DERIVATIZATION; DIASTEREOISOMER; DIELS ALDER REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY; TRANS ISOMER;

EID: 0038498498     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00368-9     Document Type: Article

References (21)

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18. (a) Busacca, C. A.; Meyers, A. I. J. Chem. Soc., Perkin Trans. 1 1991, 2299-2316. For other asymmetric Diels-Alder cycloadditions on unsaturated γ-lactams, see: (b) Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1992, 57, 1059-1061; (c) Bailey, J. H.; Cherry, D. T.; Crapnell, K. M.; Moloney, M. G.; Shim, S. B. Tetrahedron 1997, 53, 11731-11744.
19. (a) Busacca, C. A.; Meyers, A. I. J. Chem. Soc., Perkin Trans. 1 1991, 2299-2316. For other asymmetric Diels-Alder cycloadditions on unsaturated γ-lactams, see: (b) Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1992, 57, 1059-1061; (c) Bailey, J. H.; Cherry, D. T.; Crapnell, K. M.; Moloney, M. G.; Shim, S. B. Tetrahedron 1997, 53, 11731-11744.
20. (a) Busacca, C. A.; Meyers, A. I. J. Chem. Soc., Perkin Trans. 1 1991, 2299-2316. For other asymmetric Diels-Alder cycloadditions on unsaturated γ-lactams, see: (b) Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1992, 57, 1059-1061; (c) Bailey, J. H.; Cherry, D. T.; Crapnell, K. M.; Moloney, M. G.; Shim, S. B. Tetrahedron 1997, 53, 11731-11744.
21. -3. Calculations were done using the WinGX package (Farrugia, L. J. J. Appl. Cryst. 1999, 32, 837-838). CCDC deposition number 209022.