InCl₃-Catalysed Conjugate Addition of Indoles with Electron-Deficient Olefins [1]

Abstract

Indole and 2-methylindole undergo conjugate addition with electron-deficient olefins in the presence of a catalytic amount of InCl₃ at ambient temperature to afford the corresponding Michael adducts in excellent yields with high selectivity.

indium trichloride - indole - α,β-unsaturated compounds - addition reactions

References

1

IICT communication No. 4745.

2 Sundberg RJ. The Chemistry of Indoles   Academic Press; New York: 1996.  p.113 

3a Moore RE. Cheuk C. Yang XQ. Patterson GML. Bonjouklian R. Smita TA. Mynderse J. Foster RS. Jones ND. Skiartzendruber JK. Deeter JB. J. Org. Chem.  1987,  52:  1036 

3b Garnick RL. Levery SB. LeQuesne UP. J. Org. Chem.  1978,  43:  1226 

3c Moore RE. Cheuk C. Patterson GML. J. Am. Chem. Soc.  1984,  106:  6456 

4a Szmuszkovicz J. J. Am. Chem. Soc.  1957,  79:  2819 

4b Noland WE. Christensen GM. Sauer GL. Dutton GGS. J. Am. Chem. Soc.  1955,  77:  456 

4c Iqbal Z. Jackson AH. Rao KRN. Tetrahedron Lett.  1988,  29:  2577 

5a Harrington PE. Kerr MA. Synlett  1996,  1047 

5b Harrington PE. Kerr MA. Can. J. Chem.  1998,  76:  1256 

6a Loh TP. Wei LL. Synlett  1998,  975 

6b Loh TP. Pei J. Lin M. Chem. Commun.  1996,  2315 

7 Babu G. Perumal PT. Aldrichimica Acta.  2000,  33:  16