Synthesis of ω-hydroxy ketones from ω-benzyloxy weinreb amides by using a chemoselective nucleophilic addition/ birch reduction process

Organic Letters

Volumn 6, Issue 13, 2004, Pages 2145-2147

  Taillier, Catherine ^a   Bellosta, Véronique ^a   Meyer, Christophe ^a   Cossy, Janine ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; KETONE DERIVATIVE;

ADDITION REACTION; ARTICLE; BIRCH REDUCTION; CHEMICAL REACTION; DEPROTECTION REACTION; MOLECULAR STABILITY; REACTION ANALYSIS; SYNTHESIS;

EID: 3142680228     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049434f     Document Type: Article

References (15)

1. (a) Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815-3818.
2. (b) O'Neill, B. T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Schreiber, S. L., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, pp 399-407.
3. (c) Sibi, M. P. Org. Prep. Proced. Int. 1993, 25, 15-40.
4. (d) Mentzel, M.; Hoffmann, H. M. R. J. Prakt. Chem. 1997, 339, 517-524.
5. (e) Singh, J.; Satyamurthi, N.; Aidhen, I. S. J. Prakt. Chem. 2000, 342, 340-347.
6. (a) Evans, D. E.; Bender, S. L.; Morris, J. J. Am. Chem. Soc. 1988, 110, 2506-2526.
7. (b) Evans, D. A.; Rieger, D. L.; Jones, T. K.; Kaldor, S. W. J. Org. Chem. 1990, 55, 6260-6268.
8. (c) Evans, D. E.; Polniaszek, R. P.; DeVries, K. M.; Guinn, D. E.; Mathre, D. J. J. Am. Chem. Soc. 1991, 113, 7613-7630.
9. (d) Bergman, R.; Hansson, T.; Sterner, O.; Wickberg, B. Chem. Commun. 1990, 865-867.
10. (e) Bray, B. L.; Mathies, P. H.; Naef, R.; Solas, D. R.; Tidwell, T. T.; Artis, D. R.; Muchowski, J. M. J. Org. Chem. 1990, 55, 6317-6328.
11. Complete conversion of the starting amide was ascertained by TLC after aqueous workup of an aliquot.
12. (a) Shirai, F.; Nakai, T. Tetrahedron Lett. 1988, 29, 6461-6464.
13. (b) Takayama, H.; Masubuchi, K.; Kitajima, M.; Aimi, N.; Sakai, S.-I. Tetrahedron 1989, 45, 1327-1336.
14. (c) Banfi, L.; Cascio, G.; Guanti, G.; Manghisi, E.; Narisano, E.; Riva, R. Tetrahedron 1994, 41, 11967-11982.
15. (d) Yus, M.; Radivoy, G.; Alonso, F. Synthesis 2001, 914-918.