Synthesis and Diels-Alder reactions of 4-substituted-1,3-diphenoxy-2-[(tert-butyldimethylsilyl)oxy]-1,3-butadienes: Application to the synthesis of triaryl ethers

Journal of Organic Chemistry

Volumn 61, Issue 17, 1996, Pages 5852-5856

  Olsen, Richard K ^a   Shao, Rui Lian ^a  

^a UTAH STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0345034670     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960105d     Document Type: Article

References (14)

1. For views, see: (a) Petrizilka, M.; Grayson, J. I. Synthesis 1981, 753. (b) Trost, B. M., Fleming, I., Eds. Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol. 5 (Paquette, L., Ed.), Chapter 4.1, pp 329-337.
2. For views, see: (a) Petrizilka, M.; Grayson, J. I. Synthesis 1981, 753. (b) Trost, B. M., Fleming, I., Eds. Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol. 5 (Paquette, L., Ed.), Chapter 4.1, pp 329-337.
3. Olsen, R. K.; Feng, X. Tetrahedron Lett. 1991, 32, 5721.
4. Feng, X.; Olsen, R. K. J. Org. Chem. 1992, 57, 5811.
5. Olsen, R. K.; Feng, X.; Campbell, M.; Shao, R.-L.; Math, S. J. Org. Chem. 1995, 60, 6025.
6. Evans, D. A.; Ellman, J. A.; DeVries, K. M. J. Am. Chem. Soc. 1989, 111, 8912. Pearson, A. J.; Bignan, G. Tetrahedron Lett. 1996, 37, 735.
7. Evans, D. A.; Ellman, J. A.; DeVries, K. M. J. Am. Chem. Soc. 1989, 111, 8912. Pearson, A. J.; Bignan, G. Tetrahedron Lett. 1996, 37, 735.
8. Moreau, P.; Guillaumet, G.; Coudert, G. Tetrahedron 1994, 50, 3407.
9. The authors have deposited atomic coordinates, bond lengths, and angles for structure 1b with the Cambridge Crystallographic Data Centre, the data for which can be obtained, upon request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 IEZ, UK.
10. H4,H5 = 3.6 Hz.
11. Overman, L. E.; Taylor, G. F.; Houk, K. N.; Demelsmith, L. N. J. Am. Chem. Soc. 1978, 100, 3182 and references cited therein.
12. Overman, L. E.; Freerks, R. L.; Petty, C. B.; Clizbe, L. A.; Oho, R. K.; Taylor, G. F.; Jessup, P. J. J. Am. Chem. Soc. 1981, 103, 2816.
13. Danishefsky, S.; Yan, C.-F.; Singh, R. K.; Gammill, R. B.; MuCurry, P. M.; Fritsch, N.; Clardy, J. J. Am. Chem. Soc. 1979, 101, 7001.
14. Arce, E.; Carreño, M. C.; Cid, M. B.; García Ruano, J. L. J. Org. Chem. 1994, 59, 3421.