Synthesis of carboxamides by LDA-catalyzed Haller-Bauer and Cannizzaro reactions

Organic Letters

Volumn 6, Issue 12, 2004, Pages 1983-1986

  Ishihara, Kazuaki ^a   Yano, Takayuki ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; AMIDE; HYDROCARBON; KETONE DERIVATIVE; LITHIUM DERIVATIVE; LITHIUM N,N DIISOPROPYLAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; REACTION ANALYSIS;

EID: 3042790205     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0494459     Document Type: Article

References (10)

1. For reviews, see: (a) Hamlin, K. E.; Weston, A. W. Org. React. 1957, 9, 1. (b) Paquette, L. A.; Gilday, J. P. Org. Prep. Proceed. Int. 1990, 22, 167. (c) Mehta, G.; Venkateswaran, R. V. Tetrahedron 2000, 56, 1399.
2. For reviews, see: (a) Hamlin, K. E.; Weston, A. W. Org. React. 1957, 9, 1. (b) Paquette, L. A.; Gilday, J. P. Org. Prep. Proceed. Int. 1990, 22, 167. (c) Mehta, G.; Venkateswaran, R. V. Tetrahedron 2000, 56, 1399.
3. For reviews, see: (a) Hamlin, K. E.; Weston, A. W. Org. React. 1957, 9, 1. (b) Paquette, L. A.; Gilday, J. P. Org. Prep. Proceed. Int. 1990, 22, 167. (c) Mehta, G.; Venkateswaran, R. V. Tetrahedron 2000, 56, 1399.
4. 2O via dianionic species in the presence of KO-t-Bu, see: Gassman, P. G.; Lumb, J. T.; Zalar, F. V. J. Am. Chem. Soc. 1967, 89, 946.
5. Several examples of the preferential equatorial attack of alkyllithium to 2-substituted cyclohexanones have been reported: (a) Maruoka, K.; Itoh, T.; Yamamoto, H. J. Am. Chem. Soc. 1985, 107, 4573. (b) Maruoka, K.; Itoh, T.; Sakurai, M.; Nonoshita, K.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 3588.
6. Several examples of the preferential equatorial attack of alkyllithium to 2-substituted cyclohexanones have been reported: (a) Maruoka, K.; Itoh, T.; Yamamoto, H. J. Am. Chem. Soc. 1985, 107, 4573. (b) Maruoka, K.; Itoh, T.; Sakurai, M.; Nonoshita, K.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 3588.
7. Cannizzaro, S. Justus Liebigs Ann. Chem. 1853, 88, 129.
8. Ooi, T.; Tayama, E.; Yamada, M.; Maruoka, K. Synlett 1999, 729.
9. An anhydrous solution of phenylglyoxal in toluene was used. For its preparation, see the Supproting Information.
10. Rzepa, H. S.; Miller, J. J. Chem. Soc., Perkin Trans. 2 1985, 717.