General Scope of 1,3-Dioxolanation of α,β-Unsaturated Aldehydes with 1,2-Bis((trimethylsilyl)oxy)ethane and Trimethylsilyl Trifluoromethanesulfonate

Journal of Organic Chemistry

Volumn 52, Issue 2, 1987, Pages 188-191

  Hwu, Jih Ru ^a   Leu, Lish cheng ^a   Robl, Jeffrey A ^a   Anderson, Denise A ^a   Wetzel, John M ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000268520     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00378a006     Document Type: Article

References (10)

1. For general methods to prepare 1,3-dioxolanes, see: (a) Greene, T. W. Protective Groups in Organic Syntehsis, Wiley: New York, 1981; p 124. (b) Loewenthal, H. J. E. In Protective Groups in Organic Chemistry; McOmie J. F. W., Ed., Plenum: London and New York, 1973; Chapter 9.
2. Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357.
3. For the use of pyridinium p-toluenesulfonate as an efficient catalyst for the formation of dioxolane-type acetals, see: Sterzycki, R. Synthesis, 1979, 724.
4. Dann, A. E.; Davis, J. B.; Nagler, M. J. J. Chem. Soc.; Perkin Trans. 1 1979,158.
5. Chastrette, F.; Hassambay, M.; Chastrette, M. Bull. Soc. Chim. Fr. 1976, 601.
6. For a discussion of the aromatic characteristics of furan and thiophene rings, see: Acheson, R. M. An Introduction to the Chemistry of Heterocyclic Compounds, 3rd ed.; Wiley: New York 1976; pp 174–179.
7. Hwu. J. R.; Wetzel. J. M. J. Org. Chem. 1985. 50. 3946.
8. VanRheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 23, 1973.
9. House, H. 0. Modern Synthetic Reactions, 2nd ed.; Benjamin: Menlo Park, CA, 1972; pp 360–363.
10. Known compound: (a) Davis, H. A.; Brown, R. K. Can. J. Chem. 1971,49, 2563. (b) Hinz, A.; Meyer, G.; Schttcking G. Chem. Ber. 1943, 76, 676. (c) Johnson, A. L. J. Org. Chem. 1976, 41, 1320.