A new preparation of cyclopropanone hemiketals by reductive coupling of terminal olefins with ethylene carbonate

Journal of Organic Chemistry

Volumn 61, Issue 15, 1996, Pages 4878-4879

  Lee, Jinhwa ^a   Kim, Young Gyu ^b   Bae, Jae Gwang ^b   Cha, Jin Kun ^a  

^a UNIVERSITY OF ALABAMA   (United States)

^b Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000835793     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960856f     Document Type: Article

References (27)

1. For general reviews, see: (a) Turro, N. J. Acc. Chem. Res. 1969, 2, 25. (b) Wasserman, H. H.; Clark, G. M.; Turley, P. C. Top. Curr. Chem. 1974, 47, 73. (c) Wasserman, H. H.; Berdahl, D. R.; Lu, T.-J. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: Chichester, 1987; Chapter 23.
2. For general reviews, see: (a) Turro, N. J. Acc. Chem. Res. 1969, 2, 25. (b) Wasserman, H. H.; Clark, G. M.; Turley, P. C. Top. Curr. Chem. 1974, 47, 73. (c) Wasserman, H. H.; Berdahl, D. R.; Lu, T.-J. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: Chichester, 1987; Chapter 23.
3. For general reviews, see: (a) Turro, N. J. Acc. Chem. Res. 1969, 2, 25. (b) Wasserman, H. H.; Clark, G. M.; Turley, P. C. Top. Curr. Chem. 1974, 47, 73. (c) Wasserman, H. H.; Berdahl, D. R.; Lu, T.-J. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: Chichester, 1987; Chapter 23.
4. The bulky tert-butyl-disubstituted cyclopropanes are shown to be stable at room temperature: (a) Pazos, J. F.; Greene, F. D. J. Am. Chem. Soc. 1967, 89, 1030. (b) Crandall, J. K.; Machleder, W. H. J. Am. Chem. Soc. 1968, 90, 7347. (c) Camp, R. L.; Greene, F. D. J. Am. Chem. Soc. 1968, 90, 7349.
5. The bulky tert-butyl-disubstituted cyclopropanes are shown to be stable at room temperature: (a) Pazos, J. F.; Greene, F. D. J. Am. Chem. Soc. 1967, 89, 1030. (b) Crandall, J. K.; Machleder, W. H. J. Am. Chem. Soc. 1968, 90, 7347. (c) Camp, R. L.; Greene, F. D. J. Am. Chem. Soc. 1968, 90, 7349.
6. The bulky tert-butyl-disubstituted cyclopropanes are shown to be stable at room temperature: (a) Pazos, J. F.; Greene, F. D. J. Am. Chem. Soc. 1967, 89, 1030. (b) Crandall, J. K.; Machleder, W. H. J. Am. Chem. Soc. 1968, 90, 7347. (c) Camp, R. L.; Greene, F. D. J. Am. Chem. Soc. 1968, 90, 7349.
7. Salaün, J. Chem. Rev. 1983, 83, 619.
8. 1-Siloxy-1-alkoxycyclopropanes have been utilized as the homoenolate anion precursors: Kuwajima, I.; Nakamura, E. Top. Curr. Chem. 1990, 155, 1.
9. Among these methods are addition of diazoalkanes to ketenes in the presence of an alcohol, acyloin-type cyclization of 3-chloropropanoate, and the Simmons-Smith cyclopropanation of ketene trimethylsilyl ketals.
10. (a) Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 4198.
11. See also: (b) Lee, J.; Kang, C. H.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 291. (c) Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919.
12. See also: (b) Lee, J.; Kang, C. H.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 291. (c) Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919.
13. (a) Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Pritytskaya, T. S. Zh. Org. Khim. 1989, 25, 2244.
14. (b) Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Savchenko, A. I.; Pritytskaya, T. S. Zh. Org. Khim. 1991, 27, 294.
15. (c) Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A. Synthesis 1991, 234.
16. (d) Kulinkovich, O. G.; Vasilevskii, D. A.; Savchenko, A. I.; Sviridov, S. V. Zh. Org. Khim. 1991, 27, 1428.
17. (e) For use of tributyl vanadate, see: Kulinkovich, O. G.; Sorokin, V. L.; Kel'in, A. V. Zh. Org. Khim. 1993, 29, 66.
18. (a) de Meijere, A.; Kozhushkov, S. I.; Spaeth, T.; Zefirov, N. S. J. Org. Chem. 1993, 58, 502.
19. (b) See also: Chaplinski, V.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 413.
20. (a) The product 4 was obtained as a single diastereomer, and the indicated stereochemical assignment was made on the basis of difference NOE measurements. (b) The stereochemistry of the products 6a-c was assigned on the basis of difference NOE measurements; NOEs from the cyclopropane ring protons, including the -OH proton, provided a reliable guide to their stereochemical assignment. (c) Hemiketals 7-10 were obtained as a 4:1-5:1 mixture of the β-H and α-H diastereomers.
21. More recently, we discovered that use of cyclopentylmagnesium chloride (rather than cyclohexylmagnesium chloride) provides uniformly higher yields of cyclopropanols from alkyl carboxylates: Lee, J.; Cha, J. K. Unpublished results.
22. 4. Filtration and evaporation in vacuo gave the crude product. Purification by column chromatography on silica gel afforded 0.14 g (47%) of hemiketal 6a,b as a 2:1 diastereomeric mixture (a colorless oil).
23. Cf. (a) Osborne, N. F. J. Chem. Soc., Perkin Trans. 1 1982, 1435. (b) Rüchardt, C.; Eichler, S.; Panse, P. Angew. Chem., Int. Ed. Engl. 1963, 2, 619.
24. Cf. (a) Osborne, N. F. J. Chem. Soc., Perkin Trans. 1 1982, 1435. (b) Rüchardt, C.; Eichler, S.; Panse, P. Angew. Chem., Int. Ed. Engl. 1963, 2, 619.
25. A tandem application of our cyclopropanation protocol and Wittig olefination thus provides a new, convenient synthetic method for alkylidenecyclopropanes.
26. (a) Very recently, Sato and co-workers reported the identical reaction of 12, in which the γ-lactone 14 was obtained in 92% yield with use of i-PrMgCl at -40°C: Okamoto, S.; Kasatkin, A.; Zubaidha, P. K.; Sato, F. J. Am. Chem. Soc. 1996, 118, 2208. Under Sato's reaction conditions, we believe the actual product was also ester 15, which underwent facile lactonization during workup with 3 N HCl.
27. (b) Indeed, in our hands, the experimental procedure of Sato gave 70% of 15 and 4% of 14, when the reaction was quenched with addition of water in lieu of 3 N HCl. Moreover, treatment of 15 with 3 N HCl at room temperature gave the lactone 14 in quantitative yield.