[4 + 3] cycloaddition of cyclopropanone hemiacetals

Organic Letters

Volumn 3, Issue 18, 2001, Pages 2891-2893

  Cho, Sung Yun ^a   Lee, Hyoung Ik ^a   Cha, Jin Kun ^a  

^a UNIVERSITY OF ALABAMA   (United States)

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ARTICLE;

EID: 0011966007     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016354s     Document Type: Article

References (20)

1. Part 16 in the series of synthetic studies on [4 + 3] cycloadditions of oxyallyls. See also: (a) Part 15. Lee, K.; Cha, J. K. Tetrahedron Lett. 2001, 42, 6019.
2. (b) Part 14. Lee, K.; Cha, J. K. J. Am. Chem. Soc. 2001, 123, 5590.
3. (c) Part 13. Lee, J. C.; Cha, J. K. J. Am. Chem. Soc. 2001, 123, 3243.
4. For reviews, see: (a) Turro, N. J. Acc. Chem. Res. 1969, 2, 25.
5. (b) Wasserman, H. H.; Clark, G. M.; Turley, P. C. Top. Curr. Chem. 1974, 47, 73.
6. Wasserman, H. H.; Berdahl, D. R.; Lu, T.-J. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: New York, 1987; Chapter 23.
7. For reviews on oxyallyls, see: (a) Noyori, R.; Hayakawa, Y. Org. React. 1983, 29, 163.
8. (b) Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 1.
9. Mann, J. Tetrahedron 1986, 42, 4611.
10. Rigby, J. H.; Pigge, F. C. Org. React. 1997, 51, 351.
11. (e) Harmata, M. Tetrahedron 1997, 53, 6235.
12. For a comprehensive review, see: Salaün, J. Chem. Rev. 1983, 83, 619.
13. Compare p 629 and footnote 137 of ref 4.
14. Taken in part from: Cho, S. Y., Ph.D. dissertation, The University of Alabama, 2000.
15. Lee, J.; Kim, Y. G.; Bae, J. G.; Cha, J. K. J. Org. Chem. 1996, 61, 4878.
16. 2-OH: (a) Herter, R.; Föhlisch, B. Synthesis 1982, 976.
17. (b) Sendelbach, S.; Schwetzler-Raschke, R.; Radl, A.; Kaiser, R.; Henle, G. H.; Korfant, H.; Reiner, S.; Föhlisch, B. J. Org. Chem. 1999, 64, 3398 and references therein. See also:
18. Jin, S.-j.; Choi, J.-R.; Oh, J.; Lee, D.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 10914.
19. 1b (10) It is presumed that the [4 + 3] cycloaddition proceeds via cyclopropanone or ring-opened oxyallyl.
20. 3Si 281.1599, found 281.1573.