Chiral C2-symmetric Cu(II) complexes as catalysts for enantioselective intramolecular Diels-Alder reactions. Asymmetric synthesis of (-)-isopulo'upone

Journal of Organic Chemistry

Volumn 62, Issue 4, 1997, Pages 786-787

  Evans, David A ^a   Johnson, Jeffrey S ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MARINE TOXIN; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; STEREOCHEMISTRY;

EID: 0030947807     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962187b     Document Type: Article

References (25)

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2. For recent reviews, see: (a) Ishihara, K.; Yamamoto, H. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI Press: Greenwich, CT, 1995; Vol. 1, pp 29-59. (b) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007-1019.
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9. (a) Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460-6461.
10. (b) Evans, D. A.; Lectka, T.; Miller, S. J. Tetrahedron Lett. 1993, 34, 7027-7030.
11. Evans, D. A.; Murry, J. A.; Kozlowski, M. C. J. Am. Chem. Soc. 1996, 118, 5814-5815.
12. Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726-728. The synthesis of the (S,S)-bis-(oxazoline) ligand, as well as its enantiomer, is provided in the Supporting Information.
13. Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798-800.
14. Prepared from Octa-5(E),7-dienenitrile: Roush, W. R.; Gillis, H. R.; Ko, A. I. J. Am. Chem. Soc. 1982, 104, 2269-2283. Details of the synthesis and characterization of all compounds can be found in the Supporting Information.
15. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238-1256.
16. 2. The resulting heterogeneous mixture was stirred for 12 h in the absence of light and then filtered through Celite and cotton into a dry flask; the resulting blue solution was used as a 0.019 M catalyst solution. Cycloaddition. To 309 mg (0.734 mmol, 1.0 equiv) of trienimide 10 was added via syringe 2 mL (0.037 mmol, 0.05 equiv) of the catalyst solution. After 24 h at room temperature, the reaction solution was filtered through a plug of silica gel, eluting with diethyl ether. The product and starting material were separated by flash chromatography (15% EtOAc/hexanes) to afford 251 mg (81%) of 11 as a clear oil, followed by 25.5 mg (8%) of 10.
17. See the Supporting Information for details on stereochemical proofs.
18. Spinella, A.; Alvarez, L. A.; Cimino, G. Tetrahedron 1993, 49, 3203-3210. A racemic synthesis of isopulo'upone has appeared: Matikainen, J.; Kaltia, S.; Hase, T. Synth. Commun. 1995, 25, 195-201.
19. Spinella, A.; Alvarez, L. A.; Cimino, G. Tetrahedron 1993, 49, 3203-3210. A racemic synthesis of isopulo'upone has appeared: Matikainen, J.; Kaltia, S.; Hase, T. Synth. Commun. 1995, 25, 195-201.
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25. The author has deposited atomic coordinates for 4b and 13 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CH2 1EZ, UK.