A one-pot, base-free annelation approach to α-alkylidene- γbutyrolactones

Organic Letters

Volumn 11, Issue 22, 2009, Pages 5338-5341

  Kitson, Russell R A ^a   Taylor, Richard J K ^a   Wood, John L ^b  

^a UNIVERSITY OF YORK   (United Kingdom)

^b Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; GAMMA BUTYROLACTONE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

4-BUTYROLACTONE; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 70749120866     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902191d     Document Type: Article

References (17)

1. For comprehensive reviews, see: (a) Hoffman, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94.
2. (b) Kitson, R. R. A.; Millemaggi, A.; Taylor, R. J. K. Angew. Chem., Int. Ed. 2009, in press. For other recent reviews, see:
3. Schall, A.; Reiser, O. Eur. J. Org. Chem. 2008, 12, 31.
4. Feray, L.; Bertrand, M. P. Targets Heterocycl. Syst. 2008, 12, 31.
5. (a) Edwards, M. G.; Kenworthy, M. N.; Kitson, R. R. A.; Scott, M. S.; Taylor, R. J. K. Angew. Chem., Int. Ed. 2008, 47, 1935.
6. (b) Edwards, M. G.; Kenworthy, M. N.; Kitson, R. R. A.; Scott, M. S.; Whitwood, A. C.; Taylor, R. J. K. Eur. J. Org. Chem. 2008, 4769.
7. English, B. J.; Williams, R. M. Tetrahedron Lett. 2009, 50, 2713.
8. (a) Bestmann, H. J.; Sandmeier, D. Angew. Chem., Int. Ed. Engl. 1975, 14, 634.
9. (b) Bestmann, H. J.; Sandmeier, D. Chem. Ber. 1980, 113, 274.
10. Schobert, R. Org. Synth. 2005, 82, 140.
11. For recent applications, see: Boeckman, R. K., Jr.; Song, X.; Pero, J. E. J. Org. Chem. 2006, 71, 8969, and references therein.
12. For the conjugate addition of phosphoranes and related processes, see: Abdou, W. M.; Ganoub, N. A. F.; Mahran, M. R. Phosphorus, Sulfur Silicon Relat. Elem. 1992, 66, 79, and references therein.
13. Danishefsky, S. J.; Simoneau, B. J. Am. Chem. Soc. 1989, 111, 2599.
14. Ruchardt, C.; Panse, P.; Eichler, S. Chem. Ber. 1967, 100, 1144.
15. Phosphorane lactone 17 could be obtained in near quantitative yield by working-up the reaction prior to addition of the aldehyde.
16. Details have been deposited at the Cambridge Crystallography Data Centre (CCDC-741196).
17. Schroete, S. H.; Appel, R.; Brammer, R.; Schuck, G. O. Justus Liebigs Ann. Chem. 1966, 697, 42.