Asymmetric Diels-Alder cycloaddition of a di-P-stereogenic dienophile with cyclopentadiene

Tetrahedron Asymmetry

Volumn 20, Issue 9, 2009, Pages 1081-1085

  Vinokurov, Nikolai ^a   Michal Pietrusiewicz, K ^b   Butenschön, Holger ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^b MARIA CURIE SK ODOWSKA UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTADIENE DERIVATIVE; NORBORNENE DERIVATIVE; TITANIUM CHLORIDE; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CRYSTALLIZATION; CRYSTALLOGRAPHY; CYCLOADDITION; DIASTEREOISOMER; DIELS ALDER REACTION; PRIORITY JOURNAL; SEPARATION TECHNIQUE; STEREOCHEMISTRY;

EID: 65549094476     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.03.022     Document Type: Article

References (43)

1. In: de Vries J.G., and Elsevier C.J. (Eds). The Handbook of Homogeneous Hydrogenation Vols. 1-3 (2006), Wiley-VCH, Weinheim
2. Knowles W.S. Angew. Chem. 114 (2002) 2096-2107
3. Ikariya T., and Blacker A.J. Acc. Chem. Res. 40 (2007) 1300-1308
4. Brunner H. Synthesis (1988) 645-654
5. Johnson N.B., Lennon I.C., Moran P.H., and Ramsden J.A. Acc. Chem. Res. 40 (2007) 1291-1299
6. Shimizu H., Nagasaki I., Matsumura K., Sayo N., and Saito T. Acc. Chem. Res. 40 (2007) 1385-1393
7. Klingler F.D. Acc. Chem. Res. 40 (2007) 1367-1376
8. Jaekel C., and Paciello R. Chem. Rev. (Washington, DC, US) 106 (2006) 2912-2942
9. Glueck D.S. Chem. Eur. J. 14 (2008) 7108-7117
10. Tang W., and Zhang X. Chem. Rev. 103 (2003) 3029-3069
11. Pietrusiewicz K.M., and Zablocka M. Chem. Rev. 94 (1994) 1375-1411
12. Crepy K.V.L., and Imamoto T. Adv. Synth. Catal. 345 (2003) 79-101
13. Crepy K.V.L., and Imamoto T. Top. Curr. Chem. 229 (2003) 1-40
14. Aw B.-H., and Leung P.-H. Tetrahedron: Asymmetry 5 (1994) 1167-1170
15. Leung P.-H., Selvaratnam S., Cheng C.R., Mok K.F., Rees N.H., and McFarlane W. Chem. Commun. (1997) 751-752
16. Yeo W.-C., Chen S., Tan G.-K., and Leung P.-H. J. Organomet. Chem. 692 (2007) 2539-2547
17. Nagel U., and Krink T. Chem. Ber. 126 (1993) 1091-1100
18. Nagel U., and Krink T. Chem. Ber. 128 (1995) 309-316
19. Brunner H., Muschiol M., and Zabel M. Synthesis (2008) 405-408
20. Brunner H., and Pieronczyk W. Angew. Chem. 91 (1979) 655-656
21. Brandi A., Chicchi S., Goti A., Pietrusiewicz K.M., Zablocka M., and Wisniewski W. J. Org. Chem. 56 (1991) 4383-4388
22. Brandi A., Cannavo P., Pietrusiewicz K.M., Zablocka M., and Wieczorek M. J. Org. Chem. 54 (1989) 3073-3077
23. Brandi A., Cicchi S., Goti A., and Pietrusiewicz K.M. Tetrahedron: Asymmetry 2 (1991) 1063-1074
24. Goti A., Cicchi S., Brandi A., and Pietrusiewicz K.M. Tetrahedron: Asymmetry 2 (1991) 1371-1378
25. Demchuk O.M., Pietrusiewicz K.M., Michrowska A., and Grela K. Org. Lett. 5 (2003) 3217-3220
26. Vinokurov N., Michrowska A., Szmigielska A., Drzazga Z., Wojciuk G., Demchuk O.M., Grela K., Pietrusiewicz K.M., and Butenschön H. Adv. Synth. Catal. 348 (2006) 931-938
27. Vinokurov N., Garabatos-Perera J.R., Zhao-Karger Z., Wiebcke M., and Butenschön H. Organometallics 27 (2008) 1878-1886
28. Vinokurov N., Pietrusiewicz K.M., Frynas S., Wiebcke M., and Butenschön H. Chem. Commun. (2008) 5408-5410
29. Brunner H., Pieronczyk W., Schoenhammer B., Streng K., Bernal I., and Korp J. Chem. Ber. 114 (1981) 1137-1149
30. Liu D., and Zhang X. Eur. J. Org. Chem. (2005) 646-649
31. P,5S,6S)-endo-5-exo-6-di(methylphenylphosphanoyl)bicyclo[2.2.1]hept-2-ene. However, a literature (SciFinder) search revealed that the closely related NORPHOS system is commonly numbered as C-2 and C-3 being the P substituted carbon atoms, the olefinic carbon atoms being C-5 and C-6. In order to correspond to the current literature practise, this numbering scheme is also applied here.
32. CCDC 716060 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
33. Yates P., and Eaton P. J. Am. Chem. Soc. 82 (1960) 4436-4437
34. Poll T., Metter J.O., and Helmchen G. Angew. Chem. 97 (1985) 116-118
35. Walborsky H.M., Barash L., and Davis T.C. Tetrahedron 19 (1963) 2333-2351
36. Maffei M., and Buono G. New J. Chem. 12 (1988) 923-930
37. Sauer J., and Kredel J. Tetrahedron Lett. 7 (1966) 731-736
38. Brandi A., Cicchi S., Goti A., and Pietrusiewicz K.M. Phosphorus, Sulfur Silicon Relat. Elem. 75 (1993) 155-158
39. Pietrusiewicz K.M. Phosphorous, Sulfur and Silicon 109/110 (1996) 573-576
40. Pietrusiewicz K.M., Wisniewski W., Wieczorek W., and Brandi A. Phosphorous, Sulfur, Silicon Relat. Elem. 101 (1995) 253-259
41. Pietrusiewicz K.M., Zablocka M., Wieczorek W., and Brandi A. Tetrahedron: Asymmetry 2 (1991) 419-428
42. Butenschön H., Vinokurov N., Baumgardt I., and Pietrusiewicz K.M. Acta Crystallogr., Sect. E 65 (2009) o517
43. Pietrusiewicz K.M., Wisniewski W., and Zablocka M. Tetrahedron 45 (1989) 337-348