Highly efficient 1,4-addition of 1,3-diesters to conjugated enones by In/TMSCl

Journal of Organic Chemistry

Volumn 68, Issue 6, 2003, Pages 2510-2513

  Lee, Phil Ho ^a   Seomoon, Dong ^a   Lee, Kooyeon ^a   Heo, Yunkiu ^a  

^a Kangwon National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOINDIUM REAGENTS;

ADDITION REACTIONS; INDIUM; KETONES;

ESTERS;

2 CYCLOHEXENONE; BROMIDE; CYCLOPENTENONE DERIVATIVE; ESTER DERIVATIVE; INDIUM; KETONE DERIVATIVE; MALONIC ACID DERIVATIVE; MESYLIC ACID DERIVATIVE; TRIMETHANESULFONYL CHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CONJUGATION; CRYSTAL STRUCTURE; MICHAEL ADDITION; STRUCTURE ANALYSIS;

EID: 0037459682     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026600t     Document Type: Article

References (43)

1. (a) Bergman, E. D.; Ginsburg, D.; Pappo, R. Org. React. 1959, 10, 179.
2. (b) Posner, G. H. Org. React. 1972, 19, 1.
3. (c) Posner, G. H. An Introduction to Synthesis Using Organocopper Reagents; Wiley-Interscience: New York, 1980.
4. (d) Taylor, R. J. K. Synthesis 1985, 364.
5. (e) Lipshutz, B. H. Synthesis 1987, 325.
6. (f) Oare, A.; Heathcock, C. H. Topics in Stereochemistry; Interscience: New York, 1989; Vol. 19, p 227.
7. (g) Duval, D.; Geribaldi, S. The Chemistry of Enones Part 1; Interscience: New York, 1989; p 355.
8. (h) Hulce, M. Org. React. 1990, 38, 225.
9. (i) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992.
10. (j) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135.
11. (k) Taylor, R. J. K. Organocopper Reagents; Oxford University Press: Oxford, 1994.
12. (a) Nelson, J. H.; Howells, P. N.; DeLullo, G. C.; Landen, G. L.; Henry, R. A. J. Org. Chem. 1980, 45, 1246.
13. (b) Ranu, B. C.; Bhar, S. Tetrahedron 1992, 48, 1327.
14. (c) Antonioletti, R.; Bonadies, F.; Monteagudo, E. S.; Scettri, A. Tetrahedron Lett. 1991, 32, 5373.
15. (d) Baruah, B.; Boruah, A.; Prajapati, D.; Sandhu, J. S. Tetrahedron Lett. 1997, 38, 1449.
16. (e) Dauben, W. G.; Gerdes, J. M. Tetrahedron Lett. 1983, 24, 3841.
17. Huffman, J. W.; Potnis, S. M.; Satish, A. V. J. Org. Chem. 1985, 50, 4266.
18. (a) Lee, P. H.; Shim, S. C.; Kim, S. Bull. Korean Chem. Soc. 1986, 7, 425.
19. (b) Kim, S.; Lee, P. H.; Tetrahedron Lett. 1988, 29, 5413,
20. (c) Kim, S.; Lee, P. H.; Kim, S. S. Bull. Korean Chem. Soc. 1989, 10, 218.
21. (d) Kim, S.; Lee, P. H. Bull. Korean Chem. Soc. 1992, 13, 580.
22. (e) Lee, P. H.; Cho, M.; Han, I.-S.; Kim, S. Tetrahedron Lett. 1999, 40, 6975.
23. (f) Lee, P. H.; Park, J.; Lee, K.; Kim, H.-C. Tetrahedron Lett. 1999, 40, 7109.
24. (a) Lee, P. H.; Bang, K.; Lee, K.; Lee, C.-H.; Chang, S. Tetrahedron Lett. 2000, 41, 7521.
25. (b) Lee, P. H.; Lee, K.; Sung, S.-Y.; Chang, S. J. Org. Chem. 2001, 66, 8646.
26. (c) Lee, P. H.; Lee, K.; Kim, S. Org. Lett. 2001, 3, 3205.
27. (d) Lee, P. H.; Sung, S.-Y.; Lee, K. Org. Lett. 2001, 3, 3201.
28. (e) Lee, P. H.; Lee, K.; Chang, S. Synth. Commun. 2001, 31, 3189.
29. (f) Lee, P. H.; Bang, K.; Lee, K.; Sung, S.-Y.; Chang, S. Synth. Commun. 2001, 31, 3781.
30. (g) Lee, P. H.; Bang, K.; Ahn, H.; Lee, K. Bull. Korean Chem. Soc. 2001, 22, 1385.
31. (h) Lee, P. H.; Seomoon, S.; Lee, K. Bull. Korean Chem. Soc. 2001, 22, 1380.
32. (i) Bang, K.; Lee, K.; Park, Y. K.; Lee, P. H. Bull. Korean Chem. Soc. 2002, 23, 1272.
33. (j) Lee, P. H.; Sung, S.-Y.; Lee, K.; Chang, S. Synlett 2002, 146.
34. (k) Lee, K.; Seomoon, D.; Lee, P. H. Angew. Chem., Int. Ed. 2002, 41, 3901.
35. (l) Lee, K.; Lee, J.; Lee, P. H. J. Org. Chem. 2002, 67, 8265.
36. (m) Iwasawa, N.; Miura, T.; Kiyota, K.; Kusama, H.; Lee, K.; Lee, P. H. Org. Lett. 2002, 4, 4463.
37. (a) Araki, S.; Ito, Hirokazu.; Butsugan, Y. J. Org. Chem. 1988, 53, 1833.
38. (b) Araki, S.; Ito, H.; Katsumura, N.; Butsugan, Y. J. Organomet. Chem. 1989, 369, 291.
39. (c) Araki, S.; Ito, H.; Butsugan, Y. Synth. Commun. 1988, 453.
40. Wang, L.; Sun, X.; Zhang, Y. Synth. Commun. 1998, 28, 3263.
41. Araki, S.; Shimizu, T.; Jin, S.-J.; Butsugan, Y. Chem. Commun. 1991, 824.
42. Araki, S.; Horie, T.; Kato, M.; Hirashita, T.; Yamamura, H.; Kawai, M. Tetrahedron Lett. 1999, 40, 2331.
43. Lee, P. H.; Ahn, H.; Lee, K.; Sung, S.-Y.; Kim, S. Tetrahedron Lett. 2001, 42, 37.