Chemo-, regio-and stereoselective addition of nitrile oxides to cobalt-coordinated 1,3-enynes

Tetrahedron Letters

Volumn 37, Issue 25, 1996, Pages 4341-4344

  Dare, Stephanie ^a   Ducroix, Bertrand ^a   Bernard, Sophie ^a   Nicholas, Kenneth M ^a  

^a UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COBALT; NITRILE; OXAZOLINE DERIVATIVE;

ARTICLE; CHEMICAL BOND; COMPLEX FORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0030002631     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00824-6     Document Type: Article

References (19)

1. Review: Little, R.D. Thermal Cycloadditions, chap. 3.1 in vol. 5 of Comprehensive Organic Synthesis, Trost, B.M., ed., Pergamon Press: Oxford, 1992; pp. 247-266.
2. Reviews: a) Grundmann, C.; Grunanger, P. The Nitrile Oxides, Springer-Verlag, Berlin, 1971;
3. b) Torssell, K.B.G. Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis, VCH Publ., Weinheim, 1988;
4. c) Easton, C.J.; Hughes, C.M.M.; Savage, G.P.; Simpson, G.W. in Advances in Heterocyclic Chemistry, 1994, 60, 261-327, Academic Press, San Diego.
5. Ref. 2a, pp. 222-223 and references cited therein.
6. a) Chistokletov, V.N.; Troshchenko; Petrov, A.A. Zhur. Obsch. Khim. 1964, 34, 1891-1896;
7. b) Chistokletov, V.N.; Troshchenko; Petrov, A.A. ibid, 1963, 33, 2555-2559.
8. a) Nicholas, K.M.; Pettit, R. Tetrahedron Lett. 1971, 3475-3478;
9. b) Nicholas, K.M. Accts. Chem. Res. 1987, 20, 207-214;
10. c) Caffyn, A.J.M.; Nicholas, K.M., The Chemistry of Dinuclear (μ-Propargylium) Complexes, chap. 7A in vol. 12 of Comprehensive Organometallic Chemistry II, pp. 685-702, Pergamon Press, Oxford, 1995.
11. 7
12. K.M. Nicholas and R. Pettit, J. Organometal. Chem, 1972, 44, C 21-24; K.M. Nicholas, Ph. D. dissertation, U. Texas, 1972.
13. K.M. Nicholas and R. Pettit, J. Organometal. Chem, 1972, 44, C 21-24; K.M. Nicholas, Ph. D. dissertation, U. Texas, 1972.
14. Liu, K.-C.; Shelton, B.R.; Howe, R.K. J. Org. Chem. 1980, 45, 3916-3918.
15. Mukaiyama, T.; Hoshino, T. J. Am. Chem. Soc. 1960, 82, 5339-5342.
16. Chang, M.S.; Lowe, J.U. J. Org. Chem. 1967, 32, 1577-1579.
17. 1H NMR: 8.50 (s, 1H), 8.30 (d, J= 8 Hz, 1H), 8.10 (d, J= 8 Hz, 1H), 7.65 (t, J= 8 Hz, 1 H), 6.20 (s, 1H), 5.86 (d, J= 8 Hz, 1H), 3.80 (m, 1H), 0.90 (d, J = 7 Hz, 3 H); X-ray data tables for 5 are available from the Cambridge Crystallographic Data Base.
18. Caramella, P.; Albini, E.; Bandiera, T.; Coda, A.C.; Grunanger, P. Albini, F.M. Tetrahedron, 1983, 39, 689-699; Sustman, R.; Huisgen, R.; Huber, H. Chem. Ber. 1967, 100, 1802-1813.
19. Caramella, P.; Albini, E.; Bandiera, T.; Coda, A.C.; Grunanger, P. Albini, F.M. Tetrahedron, 1983, 39, 689-699; Sustman, R.; Huisgen, R.; Huber, H. Chem. Ber. 1967, 100, 1802-1813.