Direct synthesis of β-aminoketones from amides via novel sequential nucleophilic substitution/Michael reaction

Organic Letters

Volumn 2, Issue 1, 2000, Pages 11-13

  Gomtsyan, Arthur ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002603613     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9911122     Document Type: Article

References (16)

1. For a discussion of sequential transformations in organic chemistry, see: (a) Tietze, L. F. Chem. Rev. 1996, 96, 115.
2. (b) Bunce, R. A. Tetrahedron 1995, 48, 13103.
3. (c) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
4. (d) Posner, G. H. Chem Rev. 1986, 86, 831.
5. For selected examples, see: (a) Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
6. (b) Olah, G. A.; Prakash, S. G. K. S.; Arvanaghi, M. Synthesis 1984, 228.
7. For a review on the chemistry of the Weinreb amides, see: Sibi, M. P. Org. Prep. Proced. Intl. 1993, 25, 15.
8. Presented at the ACS National Meeting in New Orleans, LA, August 22-26, 1999; Abstract 513 ORG.
9. 2 194.1181, found 194.1183.
10. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992; p 114.
11. Tramontini, M. Synthesis 1973, 703.
12. For selected applications of β-aminoketones in the synthesis of natural products and biologically active compounds, see: (a) Buchi, G.; Gould, S. J.; Naf, F. J. Am. Chem. Soc. 1971, 93, 2492.
13. (b) Takahashi, K.; Shimizu, S.; Ogata, M. Synth. Commun. 1987, 17, 809.
14. (c) Ogata, M.; Matsumoto, H.; Kida, S.; Shimizu, S.; Tawara, K.; Kawamura, Y. J. Med. Chem. 1987, 30, 1497.
15. Wickberg and co-workers described the formation of unstable β-aminoketone a from the reaction of the Weinreb amide and methylcyclopropenyllithium en route to 1,4-diketones. Bergman, R.; Nilsson, B.; Wickberg, B. Tetrahedron Lett. 1990, 31, 2783. (formula presented)
16. The formation of the enolate iii (Scheme 2) could also be envisioned by bimolecular reaction of the tetrahedral internediate i. However, the experiment outlined in Scheme 4 ruled out that possibility.