Amine-catalyzed coupling of aldehydes and ketenes derived from Fischer carbene complexes: Formation of β-lactones and enol ethers

Journal of Organic Chemistry

Volumn 68, Issue 15, 2003, Pages 6056-6059

  Merlic, Craig A ^a   Doroh, Brandon C ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KETENES;

AMINES; CATALYSIS; ETHERS; PHOTOLYSIS; STEREOCHEMISTRY;

ALDEHYDES;

ALCOHOL DERIVATIVE; ALDEHYDE; AMINE; BASE; CARBENE; CHROMIUM DERIVATIVE; ETHER DERIVATIVE; KETENE DERIVATIVE; LACTONE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; DECARBOXYLATION; DIASTEREOISOMER; PHOTOLYSIS; STEREOCHEMISTRY; STOICHIOMETRY;

ALDEHYDES; AMINES; CATALYSIS; ETHYLENES; INDICATORS AND REAGENTS; KETONES; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR;

EID: 0038710552     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034476n     Document Type: Article

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10. For recent syntheses of β-lactones, see: (a) Bodkin, J. A.; Humphries, E. J.; McLeod, M. D. Tetrahedron Lett. 2003, 44, 2869. (b) Castle, K.; Hau, C.-S.; Sweeney, J. B.; Tindall, C. Org. Lett. 2003, 5, 757. (c) Molnar, F.; Luinstra, G. A.; Allmendinger, M.; Rieger, B. Chem.-Eur. J. 2003, 9, 1273. (d) Schneider, C. Angew. Chem., Int. Ed. 2002, 41, 744. (e) Cortez, G. S.; Oh, S. H.; Romo, D. Synthesis, 2001, 11, 1731. (f) Cortez, G. S.; Tennyson, R. L.; Romo, D. J. Am. Chem. Soc 2001, 123, 7945. (g) Doyle, M. P.; May, E. J. Synlett. 2001, 967. (h) Evans, D. A.; Janey, J. M. Org. Lett. 2001, 3, 2125. (i) Nelson, S. G.; Wan, Z. Org. Lett. 2000, 2, 1883. (j) Nelson, S. G.; Peelen, T. J.; Wan, Z. J. J. Am. Chem. Soc. 1999, 121, 9742. (k) Caldwell, J. J.; Kerr, W. J.; McKendry, S. Tetrahedron Lett. 1999, 40, 3485. (l) Yang, H. W.; Romo, D. Tetrahedron Lett. 1998, 39, 2877. (m) Yang, H. W.; Romo, D. J. Org. Chem. 1998, 63, 1344.
11. For recent syntheses of β-lactones, see: (a) Bodkin, J. A.; Humphries, E. J.; McLeod, M. D. Tetrahedron Lett. 2003, 44, 2869. (b) Castle, K.; Hau, C.-S.; Sweeney, J. B.; Tindall, C. Org. Lett. 2003, 5, 757. (c) Molnar, F.; Luinstra, G. A.; Allmendinger, M.; Rieger, B. Chem.-Eur. J. 2003, 9, 1273. (d) Schneider, C. Angew. Chem., Int. Ed. 2002, 41, 744. (e) Cortez, G. S.; Oh, S. H.; Romo, D. Synthesis, 2001, 11, 1731. (f) Cortez, G. S.; Tennyson, R. L.; Romo, D. J. Am. Chem. Soc 2001, 123, 7945. (g) Doyle, M. P.; May, E. J. Synlett. 2001, 967. (h) Evans, D. A.; Janey, J. M. Org. Lett. 2001, 3, 2125. (i) Nelson, S. G.; Wan, Z. Org. Lett. 2000, 2, 1883. (j) Nelson, S. G.; Peelen, T. J.; Wan, Z. J. J. Am. Chem. Soc. 1999, 121, 9742. (k) Caldwell, J. J.; Kerr, W. J.; McKendry, S. Tetrahedron Lett. 1999, 40, 3485. (l) Yang, H. W.; Romo, D. Tetrahedron Lett. 1998, 39, 2877. (m) Yang, H. W.; Romo, D. J. Org. Chem. 1998, 63, 1344.
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