A succinct method for preparing the Stork-Jung vinylsilane Robinson annulation reagent

Journal of Organic Chemistry

Volumn 70, Issue 2, 2005, Pages 739-741

  Singletary, Jeananne A ^a   Lam, Hubert ^a   Dudley, Gregory B ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SILANES; SYNTHESIS (CHEMICAL);

METHYL VINYL KETONES; STORK-JUNG VINYLSILANE REAGENTS;

KETONES;

KETONE DERIVATIVE; REAGENT; SILANE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; ROBINSON ANNULATION; SYNTHESIS;

EID: 12344254596     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0480803     Document Type: Article

References (21)

1. Rapson, W. S.; Robinson, R. J. Chem. Soc. 1935, 1285.
2. Reviews: (a) Gawley, R. E. Synthesis 1976, 777. (b) Jung, M. E. Tetrahedron 1976, 32, 3.
3. Reviews: (a) Gawley, R. E. Synthesis 1976, 777. (b) Jung, M. E. Tetrahedron 1976, 32, 3.
4. Stork, G.; Jung, M. E. J. Am. Chem. Soc. 1974, 96, 3682.
5. For a recent application of this and a related reagent, see: Snider, B. B.; Shi, B. Tetrahedron Lett. 2001, 42, 9123.
6. Stork, G.; Jung, M. E.; Colvin, E.; Noel, Y. J. Am. Chem. Soc. 1974, 96, 3684.
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11. (e) Wang, K. K.; Liu, C.; Gu, Y. G.; Burnett, F. N.; Sattsangi, P. D. J. Org. Chem. 1991, 56, 1914.
12. (a) Denmark, S. E.; Habermas, K. L.; Hite, G. A. Helv. Chim. Acta 1988, 71, 168.
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15. (b) Sato, F.; Kobayashi, Y. In Organic Syntheses; Wiley and Sons: New York, 1993; Collect. Vol. VIII, p 507.
16. A single, unoptimized example has been reported: (a) Lautens, M.; Huboux, A. H. Tetrahedron Lett. 1990, 31, 3105. (b) Lautens, M.; Zhang, C. H.; Goh, B. J.; Crudden, C. M.; Johnson, M. J. A. J. Org. Chem. 1994, 59, 6208.
17. A single, unoptimized example has been reported: (a) Lautens, M.; Huboux, A. H. Tetrahedron Lett. 1990, 31, 3105. (b) Lautens, M.; Zhang, C. H.; Goh, B. J.; Crudden, C. M.; Johnson, M. J. A. J. Org. Chem. 1994, 59, 6208.
18. (a) Two examples are described in a footnote and in undisclosed yield: Kang, J.; Cho, W.; Lee, W. K. J. Org. Chem. 1984, 49, 1838.
19. (b) For trapping with stannyl chlorides, which requires solvent exchange, see ref 9.
20. 6b although this protocol has not supplanted two-step conversions of 3 → 5. The method reported herein is advantageous in that silylation occurs without requiring the solvent exchange (vide infra), and 7 is more readily available than 3.
21. 4, although at a higher cost. See the Experimental Section.