One-pot three component synthesis of α,β-unsaturated ketones

Tetrahedron Letters

Volumn 37, Issue 51, 1996, Pages 9177-9178

  Mulzer, Johann ^a   Martin, Harry J ^a   List, Benjamin ^a  

^a GOETHE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0030590943     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02155-7     Document Type: Article

References (10)

1. 1. Reviews: a) Kelley, S.E. in Comprehensive Organic Synthesis; Trost, B.M., Ed.; Pergamon Press: Oxford 1990; Vol. 1, 729.
2. b) Maryanoff, B.E.; Reitz, A.B., Chem. Rev. 1989, 89, 863.
3. 2. For example, see: Still, W.C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405.
4. 3. Corey, E.J.; Kwiatkowski, G.T. J. Am. Chem. Soc. 1966, 88, 5654.
5. 4. For a related strategy, see: Lee, K.; Oh, Y. Synthesis 1991, 213.
6. 5. a) Lewis, C.N. et al, J. Org. Chem. 1992, 57, 1935.
7. b) Mulzer, J.; List, B. Tetrahedron Lett. 1994, 48, 9021.
8. 6. Bonadies, F.; Cardilli, A.; Lattanzi, A.; Orelli, L.R.; Scettri, A. Tetrahedron Lett. 1994, 35, 3383.
9. 3) of 3f: δ= 1.22 (d, J= 6.8, 3 H), 1.71 (d, J= 1.3, 3 H), 1.79 (m, 2 H), 2.38 (m, 2 H), 3.11 (m, 2 H), 3.75 (s, 3 H), 4.44 (d, J= 11.4, 1 H), 4.48 (d, J= 11.4, 1 H), 4.59 (d, J= 7.0, 1 H), 4.67 (d, J= 7.0, 1 H), 4.85 (q, J= 6.8, 1 H), 6.75 (dt, J= 1.3, 7.3, 1 H), 6.87 (m, 2 H), 7.23 (m, 5 H), 7.31 (m, 6 H), 7.44 (m, 6 H).
10. 8. From esters and lactones: (equation presented)