Stereoselective construction of cyclic ethers using a tandem two-component etherification: Elucidation of the role of bismuth tribromide

Journal of the American Chemical Society

Volumn 125, Issue 38, 2003, Pages 11456-11457

  Evans, P Andrew ^a   Cui, Jian ^a   Gharpure, Santosh J ^a   Hinkle, Robert J ^a,b  

^a INDIANA UNIVERSITY   (United States)

^b The College of William and Mary   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BISMUTH DERIVATIVE; BROMINE DERIVATIVE; ETHER DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYST; CHEMICAL STRUCTURE; CYCLIZATION; HYPOTHESIS; REACTION ANALYSIS; ROOM TEMPERATURE; STEREOCHEMISTRY; SYNTHESIS;

BISMUTH; BROMIDES; ETHERS, CYCLIC; STEREOISOMERISM;

EID: 0141534458     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja036439j     Document Type: Article

References (20)

1. For a review on recent advances in the stereoselective construction of C-Glycosides. see: Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913 and pertinent references therein.
2. Matano, Y.; Ikegami, T. In Organobismuth Chemistry; Suzuki, H., Matano, Y., Eds.; Elsevier: New York, 2001: Chapter 2. pp 21-245.
3. For a recent review on the uses of Bi(III) compounds in organic synthesis, see: Leonard, N. M.; Wieland, L. C.; Mohan, R. S. Tetrahedron 2002, 58, 8373.
4. (a) Komatsu, N.; Uda, M.; Suzuki, H.; Takahashi, T.; Domae, T.; Wada, M Tetrahedron Lett. 1997, 38, 7215.
5. (b) Komatsu, N.; Ishida, J.-Y.; Suzuki, H. Tetrahedron Lett. 1997, 38, 7219.
6. For an example of protodesilylation of alkyl triorganosilyl ethers using bismuth bromide, see: Bajwa, J. S.; Vivelo, J.; Slade, J.; Repic, O.; Blacklock, T. Tetrahedron Lett. 2000, 41, 6021.
7. For an example of using silyl ethers as masked hydroxyl groups, see: Angle, S. R.; El-Said, N. A. J. Am. Chem. Soc. 1999, 121, 10211.
8. For approaches to the formation of C-glycosides involving nucleophilic addition to oxocarbenium ions, see: (a) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976.
9. (b) Sassaman, M. B.; Prakash, G. K. S.; Olah, G. A. Tetrahedron 1988, 44, 3771.
10. (c) Homma, K.; Mukaiyama, T. Chem. Lett. 1989, 259 and pertinent references therein.
11. For the comparison of the kinetics of allylation of oxocarbenium ions and aldehyde Lewis acid complexes, see: Mayr, H.; Gorath, G. J. Am. Chem. Soc. 1995, 117, 7862.
12. Schelhaas, M.; Waldmann, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 2056.
13. For an example of using molecular sieves to scavenge hydrogen chloride, see: Weinstock, L. M.; Karady, S.; Roberts, F. E.; Hoinowski, A. M.; Brenner, G. S.; Lee, T. B. K.; Lumma, W. C.; Sletzinger, M. Tetrahedron Lett. 1975, 46, 3979.
14. The structure of bismuth oxybromide, isolated from the hydrolysis of bismuth bromide, was confirmed via X-ray powder diffraction.
15. Representative Experimental Procedure for the Two-Component Allylative Etherification: 6-Phenyl-5-(triethylsilyloxy)hexanal 1a (57.0 mg, 0.186 mmol) was dissolved in acetonitrile (2.0 mL) and stirred at room temperature. Bismuth tribromide (8.9 mg, 0.020 mmol) prepared as a solution in acetonitrile at 1 mg/10 μL was added via syringe directly followed by the rapid addition of allyltrimethylsilane (90 μL, 0.56 mmol). The reaction mixture was stirred at room temperature for ca. 16 h (tlc control). The solvent was removed in vacuo to afford the crude oil. Purification by flash chromatography (5% ethyl acetate/hexanes) furnished 2a (34.6 mg, 90%) as a colorless oil (ds ≥ 99:1 by GLC).
16. An alternative mechanistic proposal suggests that triethylsilyl bromide is formed from triethylsilane and bismuth tribromide and behaves as the Lewis acid catalyst, see: Bajwa, J. S.; Jiang, X.; Slade, J.; Prasad, K.; Repic, O.; Blacklock, T. J. Tetrahedron Lett. 2002, 43, 6709.
17. For a discussion of substituent effects on the stereochemical outcome of additions to tetrahydropyran derived oxocarbenium ions, see: Romero, J. A. C.; Tabacco, S. A.; Woerpel, K. A. J. Am. Chem. Soc. 2000, 122, 168.
18. 3 improved the overall efficiency. This trend is presumably a function of the ease of desilylation of the tertiary alcohol (eq 2) and increased rate of the initial intermolecular reaction in the sequential sequence (eq 3).
19. The stereochemistry of 5 was established through X-ray crystallographic analysis of the p-nitrobenzoate derivative formed through reductive ozonolysis and esterification of the intermediary alcohol.
20. For a related tandem Mukaiyama aldol-Prins cyclization cascade reaction, see: Kopecky, D. J.; Rychnovsky, S. D. J. Am. Chem. Soc. 2001, 123, 8420.