Pd-mediated cross-coupling of aryl, alkenyl, and alkynyl stannanes with chiral 2-bromo oxazolines

Tetrahedron Letters

Volumn 37, Issue 11, 1996, Pages 1747-1748

  Meyers, A I ^a   Novachek, Katherine A ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029942721     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00165-7     Document Type: Article

References (11)

1. For a recent review on oxazolines see: Gant, T. G. and Meyers, A. I. Tetrahedron, 1994, 50, 2297.
2. a) Pridgen, L. N.; Killmer, L. B. J. Org. Chem. 1981, 46, 5402. See also Wenkert, E.; Han, A. Heterocycles, 1990, 929.
3. a) Pridgen, L. N.; Killmer, L. B. J. Org. Chem. 1981, 46, 5402. See also Wenkert, E.; Han, A. Heterocycles, 1990, 929.
4. b) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A.; Pedrini, P. Synthesis, 1987, 693.
5. Leonard, W. R.; Romine, J. L.; Meyers, A. I. J. Org. Chem. 1991, 56, 1961.
6. Stang, P. J.; Treptow, W. Synthesis, 1979, 283. McMurray, J. E.; Scott, W. J. Tetrahedron Lett. 1983, 24, 79.
7. Stang, P. J.; Treptow, W. Synthesis, 1979, 283. McMurray, J. E.; Scott, W. J. Tetrahedron Lett. 1983, 24, 79.
8. Verified by X-ray crystal data analysis.
9. 2 or Ar.
10. General procedure for the cross coupling reaction: A solution of 6 was made approximately 0.5 M in the desired solvent. 1.05 equiv of the desired organostannane and 2-5 mole % of the desired catalytic reagent was added. The reaction was refluxed for 48 h after which time it was cooled and the volatiles evaporated. The residue was concentrated onto a small amount of silica gel and the product purified by silica gel flash chromatography using ethyl acetate and hexane mixtures of appropriate polarity.
11. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.