Regiocontrol in the 1,3-dipolar cycloaddition reactions of mesoionic compounds with acetylenic dipolarophiles

Tetrahedron Letters

Volumn 38, Issue 41, 1997, Pages 7159-7162

  Coppola, Brian P ^a   Noe, Mark C ^a,b   Hong, Sam Shih Kuang ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; AMPHOLYTE; PYRROLIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; STEREOCHEMISTRY;

EID: 0030658102     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01761-9     Document Type: Article

References (12)

1. Coppola, B. P.; Noe, M. C.; Abdon, R. L.; Konsler, R. L. J. Org. Chem. 1993, 58, 7324-7327.
2. Coppola, B. P.; Noe, M. C.; Schwanz, D. J.; Abdon II, R. L.; Trost, B. M. Tetrahedron 1994, 50, 93-116.
3. The pyrrole regioisomer ratios in Equation 1, originally reported in Reference 2, were inadvertently reversed in that publication and have been corrected.
4. Pizzorno, M. T.; Albonico, S. M. J. Org. Chem. 1977, 42, 909-910.
5. Beneges, I. A.; Albonico, S. M. J. Org. Chem. 1978, 43, 4273-4276.
6. Nayyar, N. K.; Hutchison, D. R.; Martinelli, M. J. J. Org. Chem. 1996, 61, 2185-2190.
7. Potts, K. T. In 1,3-Dipolar Cyloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 2; p. 7.
8. Stabilized imidazolium-based 1,3-dipoles show relatively low reactivity with DMAD (dimethyl acetylenedicarboxylate) and even slower reactions with methyl propiolate. See: Lawson, A.; Miles, D. H. J. Chem. Soc. 1959, 2865-2871.
9. Singh, G.; Pande, P. S. Tetrahedron Lett. 1974, 2169-2170.
10. Pizzorno, M. T.; Albonico, S. M. J. Org. Chem. 1974, 39, 731.
11. Coste, J.; Frérot, E.; Jouin, P. Castro, B. Tetrahedron Lett. 1991, 32, 1967-1970; and references therein.
12. Schröder, E.; Lübke, K. The Peptides Academic Press: New York, 1965; Vol. 1; pp. 144-146.