Synthesis of diastereomerically and enantiomerically pure 2,3-disubstituted tetrahydrofurans using a sulfoxonium ylide

Journal of the American Chemical Society

Volumn 126, Issue 42, 2004, Pages 13600-13601

  Schomaker, Jennifer M ^a   Pulgam, Veera Reddy ^a   Borhan, Babak ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; EPOXIDE; IODIDE; OXONIC ACID; SULFOXONIUM YLIDE; SULFUR; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CORRELATION ANALYSIS; CYCLIZATION; DIASTEREOISOMER; ENANTIOMER; EPOXIDATION; MOLECULAR DYNAMICS; MOLECULAR MECHANICS; REACTION ANALYSIS; RING OPENING; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS; TECHNIQUE; TRANS ISOMER;

EID: 6444221482     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0469075     Document Type: Article

References (22)

1. Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima I., Ed.; Wiley-VCH: New York, 1993; pp 101-158.
2. Sasaki, M.; Tanino, K.; Hirai, A.; Miyashita, M. Org. Lett. 2003, 5, 1789-1791.
3. Poch, M.; Alcon, M.; Moyano, A.; Pericas, M. A.; Riera. A. Tetrahedron Lett. 1993, 34, 7781-7784.
4. Choudary, B. M.; Rani, S. S.; Kantam, M. L. Synth. Commun. 1990, 20, 2313-2317.
5. Kirshenbaum, K. S.; Sharpless, K. B. Chem. Lett. 1987, 11-14.
6. Ko, S. Y.; Sharpless, K. B. J. Org. Chem. 1986, 51, 5413-5415.
7. Behrens, C. H.; Sharpless, K. B. J. Org. Chem. 1985, 50, 5696-5704.
8. Behrens, C. H.; Ko, S. Y.; Sharpless, K. B.; Walker, F. J. J. Org. Chem. 1985, 50, 5687-5696.
9. Caron, M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1557-1560.
10. Roush, W. R.; Brown, R. J.; Dimare, M. J. Org. Chem. 1983, 48, 5083-5093.
11. Walker, B. J. Organophosphorus Chem. 1996, 27, 264-307.
12. Vedejs. E.; Peterson, M. J. In Topics in Stereochemistry; John Wiley & Sons: New York, 1994; Vol. 21, pp 1-157.
13. Okuma, K.; Tanaka, Y.; Kaji, S.; Ohta, H. J. Org. Chem. 1983, 48, 5133-5134.
14. Fitton, A. O.; Hill, J.; Jane, D. E.; Millar, R. Synthesis 1987, 1140-1142.
15. Trost, B. M.; Melvin, L. S., Jr. Sulfur Ylides. Emerging Synthetic Intermediates; Academic Press: New York, 1975: Vol. 31.
16. Possible counterion influence in the conversion of 2 to 3 was investigated with using Li. Na, and K salts. The isolated yields of 3 LiHMDS. NaHMDS, and KHMDS as bases were 59%, 92%, and 82%, respectively. Per the suggestion of the reviewer, microwave-assisted conversion of 2 to 3 with NaHMDS as the base in DMSO greatly reduced the reaction time (30 pulses, 15 s/pulse) while maintaining a high yield of product (see Supporting Information for details).
17. Payne, G. B. J. Org. Chem. 1962, 27, 3819-3822.
18. Hanson, R. M. Org. React. 2002, 60, 1-156.
19. Wrobel, J. E.; Ganem, B. J. Org. Chem. 1983, 48, 3761-3764.
20. Rickborn, B.; Thummel, R. P. J. Org. Chem. 1969, 34, 3583-3586.
21. Alcaraz, L.; Cridland, A.; Kinchin, E. Org. Lett. 2001, 3, 4051-4053.
22. Page, P. C. B.; Rayner, C. M.; Sutherland, I. O. J. Chem. Soc., Perkin Trans. I 1990, 1375-1382.