Rhodium-catalyzed 1,4-addition of alkenylzirconocene chlorides to electron deficient alkenes

Tetrahedron

Volumn 60, Issue 6, 2004, Pages 1293-1299

  Kakuuchi, Akito ^a   Taguchi, Takeo ^a   Hanzawa, Yuji ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 BUTENOYL CHLORIDE; 2,2,5 TRIMETHYL 3 PENTADECEN 7 ONE; 2,6,6 TRIMETHYL 1 PHENYL 4 HEPTEN 1 ONE; 3 (3 METHYL 4 NONENOYL) 1,3 OXAZOLIDIN 2 ONE; 3 (3,3 DIMETHYL 1 BUTENYL)CYCLOHEPTANONE; 3 (3,6,6 TRIMETHYL 4 HEPTENOYL) 1,3 OXAZOLIDIN 2 ONE; 3 METHYL 4 NONENOYLSULTAM; 3,3,6,6 TETRAMETHYL 1 PHENYL 4 HEPTEN 1 ONE; 3,6,6 TRIMETHYL 1 (1 PIPERIDINYL) 4 HEPTEN 1 ONE; 3,6,6 TRIMETHYL 4 HEPTENOYLSULTAM; 4 ISOPROPYL 3 (3,6,6 TRIMETHYL 4 HEPTENOYL) 1,3 OXAZOLIDIN 2 ONE; 4 PHENYL 3 (3,6,6 TRIMETHYL 4 HEPTENOYL) 1,3 OXAZOLIDIN 2 ONE; 6,6 DIMETHYL 1 PHENYL 4 HEPTEN 1 ONE; 6,6 DIMETHYL 1,3 DIPHENYL 4 HEPTEN 1 ONE; 7,7 DIMETHYL 4 PHENYL 5 OCTEN 2 ONE; ALKENE DERIVATIVE; AMIDE; CHLORIDE; ESTER DERIVATIVE; ISOPROPYL 6,6 DIMETHYL 3 PHENYL 4 HEPTENOATE; METHYL 3 (3,3 DIMETHYL 1 BUTEN 1 YL)OCTANOATE; METHYL 6,6 DIMETHYL 3 PHENYL 4 HEPTENOATE; N BENZYL 3,6,6 TRIMETHYL 4 HEPTENAMIDE; OXAZOLIDINONE DERIVATIVE; RHODIUM; TERT BUTYL 6,6 DIMETHYL 3 PHENYL 4 HEPTENOATE; UNCLASSIFIED DRUG; ZIRCONOCENE;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; CONJUGATION; ELECTRON; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

GADUS MORHUA;

EID: 1642431620     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.08.073     Document Type: Article

References (34)

1. For reviews, see: (a) Perlmutter P. Conjugate Addition Reactions in Organic Synthesis. 1992;Pergamon, Oxford.
2. Schmalz H.-G. Trost B.M., Flemming I. Comprehensive Organic Synthesis. Vol. 4:1991;Pergamon, Oxford. Chapter 1.5.
3. Rossiter B.E., Swingle N.M. Chem. Rev. 92:1992;771.
4. For review, see: Fagnou K., Lautens M. Chem. Rev. 103:2003;169. and the references therein.
5. For review, see: (a) Hayashi T. Synlett. 2001;879.
6. Kakuuchi A., Taguchi T., Hanzawa Y. Tetrahedron Lett. 44:2003;923.
7. Wipf P., Kendall C., Stephenson C.R.J. J. Am. Chem. Soc. 123:2001;5122.
8. Wipf P., Kendall C. Org. Lett. 3:2001;2773.
9. Wipf P., Kendall C., Stephenson C.R. Chem. Eur. J. 8:2002;1778.
10. (d) See also: Marek I. Titanium and Zirconium in Organic Synthesis. 2002;Wiley-VCH, Weinheim.
11. Schwartz J., Labinger J.A. Angew. Chem., Int. Ed. Engl. 15:1976;333.
12. Takahashi T., Kotora M., Fischer R., Nishihara Y., Nakajima K. J. Am. Chem. Soc. 117:1995;11039.
13. Wipf P., Smitrovich J.H. J. Org. Chem. 56:1991;6494.
14. Wipf P., Smitrovich J.H., Lehmann R., Venanzi L.M. Tetrahedron. 50:1994;1935.
15. Lipshutz B.H., Wood M.R. J. Am. Chem. Soc. 116:1994;11689.
16. Loots M., Schwartz J. J. Am. Chem. Soc. 99:1977;8045.
17. Schwartz J., Loots M., Kosugi H. J. Am. Chem. Soc. 102:1980;1333.
18. Loots M.J., Dayrit F.M., Schwartz. J. Bull. Soc. Chim. Belg. 89:1980;897.
19. Dayrit F.M., Schwartz J. J. Am. Chem. Soc. 103:1981;4466.
20. For the sake of the spectral simplicity of the 1,4-addition products, we used tert-butyl acetylene as a starting alkyne for the hydrozirconation in most of the examined cases.
21. Wakasugi K., Nakamura A., Tanabe Y. Tetrahedron Lett. 42:2001;7424.
22. Knol J., Feringa B.L. Synth. Commun. 26:1996;261.
23. Sakuma S., Miyaura N. J. Org. Chem. 66:2001;8944.
24. Oi S., Moro M., Ono S., Inoue Y. Chem. Lett. 1998;83.
25. Oi S., Moro M., Ito H., Honma Y., Miyano S., Inoue Y. Tetrahedron. 58:2002;91.
26. We have also succeeded in trapping the Zr-enolate 9 (Fig. 1) by a carbon electrophile through an intramolecular aldol reaction, and the results will be published in due course.
27. Wipf P., Jahn H. Tetrahedron. 52:1996;12853.
28. Evans D.A., Chapman K.T., Bisaha J. J. Am. Chem. Soc. 110:1988;1238.
29. Nicolas E., Russell K.C., Hruby. J. Org. Chem. 58:1993;766.
30. Oppolzer W., Kingma A.J., Poli G. Tetrahedron. 58:2002;91.
31. Bernardi A., Cardani S., Poli G., Scolastico C. J. Org. Chem. 51:1986;5041.
32. Wipf P., Takahashi H. Chem. Commun. 1996;2675.
33. Reiser O. Schmalz H.-G. Organic Synthesis Highlights IV. 2000;11 Wiley-VCH, Weinheim.
34. Buchwald S.L., LaMaire S.J., Nielsen R.B., Watson B.T., King S.M. Org. Synth. 71:1993;77.