Catalytic enantioselective hetero diels-alder reactions of αβ-unsaturated acyl phosphonates with enol ethers

Journal of the American Chemical Society

Volumn 120, Issue 19, 1998, Pages 4895-4896

  Evans, David A ^a   Johnson, Jeffrey S ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001443088     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja980423p     Document Type: Article

References (20)

1. (a) Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460-6461.
2. (b) Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798-800.
3. (c) Evans, D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481-7484.
4. (d) Evans, D. A.; Barnes, D. M. Tetrahedron Lett. 1997, 38, 57-58.
5. (e) Evans, D. A.; Johnson, J. S. J. Org. Chem. 1997, 62, 786-787.
6. (f) Evans, D. A.; Shaughnessy, E. A.; Barnes, D. M. Tetrahedron Lett. 1997, 38, 3193-3194.
7. (a) Evans, D. A.; Murry, J. A. J. Am. Chem. Soc. 1996, 118, 5814-5815.
8. (b) Evans, D. A.; Kozlowski, M. C.; Burgey, C. S.; MacMillan, D. W. C. J. Am. Chem. Soc. 1997, 119, 7893-7894.
9. Formal hetero Diels-Alder reactions between electron-rich dienes and pyruvate have recently been reported with these complexes: Johannsen, M.; Jørgensen, K. A. J. Chem. Soc., Chem. Commun. 1997, 2169-2170.
10. Cycloadditions of an αβ-unsaturated acyl phosphonate with alkylidene dithianes have been reported: Schuster, T.; Evans, S. A., Jr. Phosphorous, Sulfur, Silicon 1995, 103, 259-271.
11. Hetero Diels-Alder reactions of αβ-unsaturated carbonyls with enol ethers: (a) McRae, K. J.; Rizzacasa, M. A. J. Org. Chem. 1997, 62, 1196-1197.
12. (b) Dondoni, A.; Kniezo, L.; Martinkova, M.; Imrich, J. Chem. Eur. J. 1997, 3, 424-430.
13. (c) Wada, E.; Pei, W.; Yasuoka, H.; Chin, U.; Kanemasa, S. Tetrahedron 1996, 52, 1205-1220 and references therein.
14. (d) Tietze, L. F.; Schneider, C.; Grote, A. Chem. Eur. J. 1996, 2, 139-148 and references therein.
15. (e) Gaudenzi, L. D.; Apparao, S.; Schmidt, R. R. Tetrahedron 1990, 46, 277-290 and references therein.
16. (f) Boger, D. L.; Robarge, K. D. J. Org. Chem. 1988, 53, 5796-5798.
17. (g) Boger, D. L.; Robarge, K. D. J. Org. Chem. 1988, 53, 3373-3377.
18. For general references on the hetero Diels-Alder reaction, see: (a) Boger, D. L. In ComprehensiVe Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 451-512.
19. (b) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, CA, 1987.
20. For a hetero Diels-Alder reaction between an aryl imine and cyclopentadiene, see: Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 7357-7360.