Preparation of pyrrole-2-carboxylates with electron-withdrawing groups at the 4-position

Synthesis

Volumn , Issue 3, 1999, Pages 471-474

  Uno, Hidemitsu ^a   Tanaka, Masanori ^a   Inoue, Takashi ^a   Ono, Noboru ^a  

^a EHIME UNIVERSITY   (Japan)

Author keywords

Alkenyl sulfones; Barton Zard reaction; Pyrrole 2 carboxylate; Trifluoromethyl

Indexed keywords

ALKENYL GROUP; CARBOXYLIC ACID DERIVATIVE; PORPHYRIN; PYRROLE DERIVATIVE; SULFIDE; SULFONE;

AROMATIZATION; ARTICLE; ELECTRICITY; ELECTRON; MELTING POINT; OXIDATION REDUCTION POTENTIAL; POLYMERIZATION; REACTION ANALYSIS; STEREOISOMERISM; SYNTHESIS;

EID: 0032986698     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3406     Document Type: Article

References (13)

1. Ito, S.; Murashima, T.; Ono, N. J. Chem. Soc., Perkin Trans. 1 1997, 3161, and the corresponding examples cited therein.
2. Barton, D. H. R.; Zard, S. Z. J. Chem. Soc., Chem. Commun. 1985, 1098.
3. (a) Arnord, D. P.; Burgess-Dean, L.; Hubbard, J.; Rahman, M. A. Aust. J. Chem. 1994, 47, 969.
4. (b) Uno, H.; Sakamoto, K.; Tominaga, T.; Ono, N. Bull. Chem. Soc. Jpn. 1994, 67, 1441.
5. Happer, D. A. R.; Steenson, B. E. Synthesis 1980, 806.
6. The 2,2,2-trifluoro-I-phenylsulfonylethyl carbanion generated in the presence of tetraethylammonium chloride can be alkylated with reactive halides such as methyl iodide, allyl iodide, benzyl bromide, and so on, see: Uneyama, K.; Momota, M. Bull. Chem. Soc. Jpn. 1989, 62, 3378. This carbanion, however, failed to react with aldehydes probably due to the reversible nature of such aldol-type reaction especially in the presence of an onium counter cation.
7. Alvernhe, G.; Langlois, B.; Laurent, A.; Le Drean, I.; Selmi, A. Tetrahedron Lett. 1991, 32, 643. Laurent, A.; Le Drean, I.; Selmi, A. Tetrahedron Lett. 1991, 32, 3071.
8. Alvernhe, G.; Langlois, B.; Laurent, A.; Le Drean, I.; Selmi, A. Tetrahedron Lett. 1991, 32, 643. Laurent, A.; Le Drean, I.; Selmi, A. Tetrahedron Lett. 1991, 32, 3071.
9. Dishart, K. T.; Levine, R. J. Am. Chem. Soc. 1956, 78, 2268.
10. Bégué, J. -P.; Bonnet-Delpon, D.; M'Bida, A. Tetrahedron Lett. 1993, 34, 7753.
11. Crandall, J. K.; Batal, D. J.; Sebesta, D. P.; Lin, F. J. Org Chem. 1991, 56, 1153.
12. Murashima, T.; Tamai, R.; Fujita, K.; Uno, H.; Ono, N. Tetrahedron Lett. 1996, 37, 8391. Schwesinger, R.; Hasenfratz, C.; Schlemper, H.; Walz, L.; Peters, E. -M.; Schnering, H. G. Angew. Chem., Int. Ed. Engl. 1993, 32, 1361.
13. Murashima, T.; Tamai, R.; Fujita, K.; Uno, H.; Ono, N. Tetrahedron Lett. 1996, 37, 8391. Schwesinger, R.; Hasenfratz, C.; Schlemper, H.; Walz, L.; Peters, E. -M.; Schnering, H. G. Angew. Chem., Int. Ed. Engl. 1993, 32, 1361.