C2-symmetric bissulfoximines as ligands in copper-catalyzed enantioselective Diels-Alder reactions

Organic Letters

Volumn 5, Issue 4, 2003, Pages 427-429

  Bolm, Carsten ^a   Martin, Marc ^a   Simic, Oliver ^a   Verrucci, Marinella ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; CYCLOPENTADIENE DERIVATIVE; IMINE; ION; KETONE DERIVATIVE; LIGAND; METAL; OXAZOLINE DERIVATIVE; SOLVENT;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; COMPARATIVE STUDY; CYCLOADDITION; DIELS ALDER REACTION; ENANTIOSELECTIVITY;

EID: 0038812859     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027273e     Document Type: Article

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38. 2; 10 mol % each] the reaction between 2a and 1,3-cyclohexadiene gave the corresponding product with 63% ee in 98% yield.
39. 2 were also tested and gave products with less than 35% ee
40. Significant counterion effects have also been observed in reactions with Cu(II)-BOX catalysts (for examples, see refs 10c,d).
41. We chose to use 5a in this optimization process, because it is readily available in a one-step process from commercially available starting materials. For details see ref 8.
42. Bissulfoximines of this type with stronger electron-donating substituents at C4 and C5 have remained inaccessible to date.
43. For details see the Supporting Information.
44. 2 affords cycloadducts of type 3 with enantiomeric excesses >94% at ambient temperatures. For details, see: Evans, D. A.; Barnes, D. M.; Johnson, J. S.; Lectka, T.; von Matt, P.; Miller, S.; Murry, J. A.; Norcross, R. D.; Shaughnessy, E. A.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 7582.