Enantiocontrolled synthesis of spirooxindoles based on the [5 + 2] cycloaddition of a Tp(CO)2Mo(pyridinyl) scaffold (Tp = hydridotrispyrazolylborate)

Organic Letters

Volumn 2, Issue 25, 2000, Pages 4083-4086

  Malinakova, Helena C ^a   Liebeskind, Lanny S ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; BORIC ACID; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; HYDRIDOTRISPYRAZOLYLBORATE (CO)2MO(PYRIDINYL); HYDRIDOTRISPYRAZOLYLBORATE-(CO)2MO(PYRIDINYL); INDOLE DERIVATIVE; ORGANOMETALLIC COMPOUND; OZONE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMISTRY; CYCLIZATION; HYDROLYSIS; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; BORATES; CYCLIZATION; HYDROLYSIS; INDICATORS AND REAGENTS; INDOLES; ORGANOMETALLIC COMPOUNDS; OZONE; PYRROLIDINES; STEREOISOMERISM;

EID: 0034649731     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000313z     Document Type: Article

References (30)

1. (a) Liu, R.-S.; Li, C.-L. Chem. Rev. 2000, 100(8), 3127-3162.
2. (b) Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 1999, 121(24), 5811-5812.
3. Malinakova, H. C.; Liebeskind, L. S. Org. Lett., in press.
4. For alstonia alkaloids, see: (a) Atta-ur-Rahman, Qureshi, M. M.; Muzaffar, A. Heterocycles 1988, 27(3), 725-732.
5. For spirotryprostatins, see: (b) Cui, C-B.; Kakeya, H.; Okada, G.; Onose, R.; Osada, H. J. Antibiot. 1996, 49, 527-533.
6. Edmondson, S. E.; Danishefsky, S. J.; Sepp-Lorenzino, L.; Rosen, N. J. Am. Chem. Soc. 1999, 121(10), 2147-2155.
7. (a) von Nussbaum, F.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2000, 39(12), 2175-2178.
8. (b) Sebahar, P. R.: Williams, R. M. J. Am. Chem. Soc. 2000, 122(23), 5666-5667.
9. (c) Wang, H.; Ganesan, A. J. Org. Chem. 2000, 65(15), 4685-4693.
10. (d) Edmondson, S. D.: Danishefsky, S. J. Angew. Chem., Int. Ed. 1998, 37(8), 1138-1140.
11. Hinman, R. L.; Bauman, C. P. J. Org. Chem. 1964, 29, 2431-2437.
12. The β-substituted analogues of methylenoxindole 2 have been used in the classical [3 + 2] cycloadditions of azomethine ylides, see: (a) Wenkert, E.; Liu, S. Synthesis 1992, 323-327.
13. (b) Autrey, R. L.; Tahk, F. C. Tetrahedron 1967, 23, 901-917.
14. Petrounia, I. P.; Goldberg, J.; Brush, E. J. Biochemistry 1994, 33(10), 2891-2899.
15. Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Synlett 1993, 472-474.
16. 3) δ 228.6, 227.9, 181.7, 154.7, 146.3, 144.9, 142.0, 140.8, 140.0. 136.5, 136.0, 134.5, 129.2, 128.8, 126.2, 121.8, 110.1, 105.8, 105.7, 105.7, 64.4, 60.0, 59.0, 58.4, 56.8, 54.7, 52.7, 43.4.
17. 3 catalysis, the [5 + 2] cycloaddition of the complex (±)-1 with the stable β-substituted oxindoles shown below did not afford improved yields of the cycloadducts. (matrix presented)
18. 3 (0.27 equiv) was used as the catalyst. (matrix presented) (±)-1 (30% recovery) (37 %)
19. Moretto, A. F.; Liebeskind, L. S. J. Org. Chem. 2000, 65(22), 7445-7455.
20. Pham, V. C.; Charlton, J. L. J. Org. Chem. 1995, 60(24), 8051-8055.
21. Rawal, V. H.; Michoud, C. J. Org. Chem. 1993, 58(21), 5583-5584.
22. (a) Yu, P.; Cook, J. M. Tetrahedron Lett. 1997, 38(51), 8799-8802.
23. (b) Hollinshead, S. P.; Grubisha, D. S.; Bennett, D. W.; Cook, J. M. Heterocycles 1989, 29(3), 529-537.
24. Personal communication from Professor James Cook, University of Wisconsin at Milwaukee.
25. Gemal, A. L.; Luche, J.-L. J. Am. Chem. Soc. 1981, 103(18), 5454-5469.
26. Krief, A.: Surleraux, D.; Frauenrath, H. Tetrahedron Lett. 1988, 47, 6157-6160.
27. 13C NMR data of (±)-7 are highly complex, showing two sets of signals for each carbon and proton at room temperature. Increasing the temperature for the NMR experiments to 60 °C resulted in significant peak broadening.
28. Brown. H. C.: Krishnamurthy, S. J. Am. Chem. Soc. 1972, 94(20), 7159-7161.
29. Clark, R. D.; Heathcock, C. H. J. Org. Chem. 1976, 41(8), 1396-1403.
30. The structures of compounds (+)-4, (+)-7, (-)-8, shown in Scheme 3, correspond to the mirror images of the actual enantiomers.