Tributylphosphine-Catalyzed Acylations of Alcohols: Scope and Related Reactions

Journal of Organic Chemistry

Volumn 58, Issue 25, 1993, Pages 7286-7288

  Vedejs, E ^a   Bennett, N S ^a   Conn, L M ^a   Diver, S T ^a   Gingras, M ^a   Lin, S ^a   Oliver, P A ^a   Peterson, M J ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33751386272     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00077a064     Document Type: Note

References (24)

1. Vedejs, E.; Diver, S. J. Am. Chem. Soc. 1993, 115, 3358.
2. Höfle, G.; Steglich, W.; Vorbrüggen, H. Angew. Chem., Int. Ed. Engl. 1978, 17, 569.
3. Scriven, E. F. V. Chem. Soc. Rev. 1984, 12, 124.
4. Höfle, G.; Steglich, W. Synthesis 1972, 619.
5. DMAP + DCCD: Neises, B.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 522.
6. Hassner, A.; Alexanian, V. Tetrahedron Lett. 1978, 19, 4475.
7. Sweet, D. V. Registry of Toxic Effects of Chemical Substances 1985–86; U.S. Govt. Printing Office: Washington, DC, 1988; p 3336, 4049.
8. Buckler, S. A. J. Am. Chem. Soc. 1962, 84, 3093.
9. Hojo, K.; Yoshino, H.; Mukaiyama, T. Chem. Lett. 1977, 133.
10. Thiol esters using DMAP: Kawanami, Y.; Dainobu, Y.; Inananga, J.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1981, 54, 943.
11. Theisen, P. D.; Heathcock, C. H. J. Org. Chem. 1993, 58, 142.
12. Theisen, P. D.; Heathcock, C. H. J. Org. Chem. 1988, 53, 2374.
13. Kimel, W.; Cope, A. C. J. Am. Chem. Soc. 1943, 65, 1992.
14. DMAP + diketene: Wilson, S. R.; Price, M. F. J. Org. Chem. 1984, 49, 722.
15. Triphenylphosphine catalysis in the diketene reaction is also reported (refluxing methanol: Probst, O.; Hornig, L., Br. Pat. 1175240, 1972;
16. Chem. Abstr. 1971, 74, 31553).
17. Cristol, S. J.; Lee, G. A.; Noreen, A. L. J. Am. Chem. Soc. 1973, 95, 7067.
18. Noda, K.; Nakagawa, A.; Hirano, M.; Miyata, S.; Nakajima, I.; Ide, H. Jpn. Kokai Tokkyo koho 1978, 78 82, 761;
19. Chem. Abstr. 1979, 90, 38721.
20. Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1979, 18, 707.
21. Kim, S.; Lee, J. I.; Kim, Y. C. J. Org. Chem. 1985, 50, 560.
22. For DMAP catalysis in silylations, see: Chaudhary, S. K.; Hernandez, O. Tetrahedron Lett. 1979, 20, 99.
23. Hwang, C. K.; Li, W. S.; Nicolaou, K. C. Tetrahedron Lett. 1984, 25, 2295.
24. Bezrodnyi, V. P.; Skrypnik, Y. G.; Lyaschuk, S. N.; Byalikh, E. V. Zh. Org. Khim. 1989, 25, 1732.