Synthesis and dienophilic behavior of enantiomerically pure (E)-2-p-tolylsulfinylacrylonitrile derivatives

Tetrahedron Asymmetry

Volumn 13, Issue 18, 2002, Pages 2003-2010

  García Ruano, José L ^a   González Gutiérrez, Lorena ^a   Martín Castro, Ana M ^a   Yuste, Francisco ^a  

^a Dpto Ciencias de la Salud URJC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 [(4 METHYLPHENYL)SULFINYL] 4 OXOBUT 2 ENENITRILE; 4,4 DIETHOXY 2 [(4 METHYLPHENYL)SULFINYL]BUT 2 ENENITRILE; CYCLOPENTADIENE DERIVATIVE; NITRILE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DIELS ALDER REACTION; ENANTIOMER; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037145035     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00540-2     Document Type: Article

References (21)

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13. 1H NMR spectra of the crude product obtained under these conditions do not reveal the presence of compound 10, but a small amount of it was isolated by chromatography - as a mixture of 7 and 10 - and therefore, it has been included in entry 12 ( Table 2 ).
14. The authors have deposited the atomic coordinates for 7 with the Cambridge Crystallographic Data Centre (Deposit No. CCDC 188910). The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.
15. H 7.84 and 7.36 (AA′BB′ system, 4H), 6.48 (dd, 1H, J 3.4 and 5.7), 6.29 (dd, 1H, J 3.0 and 5.7), 4.44 (d, 1H, J 7.5), 3.73-3.49 (m, 4H), 3.42-3.25 (m, 2H), 3.15-3.10 (m, 1H), 2.56 (dd, 1H, J 2.2 and 7.5), 2.45 (s, 3H), 1.96 (d, 1H, J 9.7), 1.66 (d, 1H, J 9.7), 1.22 (t, 3H, J 7.1), 0.81 (t, 3H, J 7.1).
16. Double Pulsed Field Gradient Echo-DPFGS (Bruker DRX-500). NOE values for endo-7: 3.5% [C(3)H-C(7)H]; endo-8: 2.7% [C(3)H-C(7)H]; exo-9: 1.8% [C(3)H-C(5)H].
17. All reactions performed for longer reaction times or those consisting in treating any of the adducts 4-6 under the reaction conditions optimized for the cycloaddition, did not give any evidence of retro Diels-Alder reaction.
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