Synthesis of enantioenriched homopropargylic sulfonamides by a three component reaction of aldehydes, sulfonamides, and chiral allenylsilanes

Organic Letters

Volumn 11, Issue 19, 2009, Pages 4362-4365

  Brawn, Ryan A ^a   Panek, James S ^a  

^a Boston University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; DRUG DERIVATIVE; PARGYLINE; SILANE DERIVATIVE; SULFONAMIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; MOLECULAR STRUCTURE; PARGYLINE; SILANES; STEREOISOMERISM; SULFONAMIDES;

EID: 70350167146     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901692n     Document Type: Article

References (25)

1. For recent reviews on allene chemistry, see: (a) Hassan, H. H. A. M. curr. Org. Synth. 2007, 4, 413-439.
2. (b) Ma, S. Chem. Rev. 2005, 105, 2829-2872.
3. (c) Zimmer, R.; Dinesh, C. U.; Nandanan, E.; Khan, F. A. Chem. Rev. 2000, 100, 3067-3125.
4. (a) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878.
5. (b) Marshall, J. A.; Maxson, K. J. Org. Chem. 2000, 65, 630-633.
6. Brawn, R. A.; Panek, J. S. Org. Lett. 2007, 9, 2689-2692.
7. Danheiser, R. L.; Stoner, E. J.; Koyama, H.; Yamashita, D. S.; Klade, C. A. J. Am. Chem. Soc. 1989, 111, 4407-4413.
8. Danheiser, R. L.; Kwasigroch, C. A.; Tsai, Y.-M. J. Am. Chem. Soc. 1985, 107, 7233-7235.
9. Brawn, R. A.; Panek, J. S. Org. Lett. 2009, 11, 473-476.
10. (a) Fuchibe, K.; Hatemata, R.; Akiyama, T. Tetrahedron Lett. 2005, 46, 8563-8566.
11. (b) Daidouji, K.; Fuchibe, K.; Akiyama, T. Org. Lett. 2005, 7, 1051-1053.
12. (a) Yamamoto, Y.; Ito, W.; Maruyama, K. J. Chem. Soc, Chem. Commun. 1984, 1004-1005.
13. (b) Nikam, S. S.; Wang, K. K. J. Org. Chem. 1985, 50, 2193-2195.
14. (c) Brown, H. C.; Khire, U. R.; Narla, G.; Racherla, U. S. J. Org. Chem. 1995, 60, 544-549.
15. Gonzalez, A. Z.; Soderquist, J. A. Org. Lett. 2007, 9, 1081-1084.
16. (a) Panek, J. S.; Jain, N. F. J. Org. Chem. 1994, 59, 2674-2675.
17. (b) Schaus, J. V.; Jain, N.; Panek, J. S. Tetrahedron 2000, 56, 10263-10274.
18. (c) Lipomi, D. J.; Panek, J. S. Org. Lett. 2005, 7, 4701-4704.
19. (d) Berger, R.; Rabbat, P. M. A.; Leighton, J. L. J. Am. Chem. Soc. 2003, 125, 9596-9597.
20. (e) Shirakawa, S.; Berger, R.; Leighton, J. L. J. Am. Chem. Soc. 2004, 127, 2858-2859.
21. (f) Veenstra, S. J.; Schmid, P. Tetrahedron Lett. 1997, 38, 997-1000.
22. (g) Phukan, P. J. Org. Chem. 2004, 69, 4005-4006.
23. In addition to carbamates and sulfonamides, benzylamines, allylamines, acetamides, and anilines were screened, but all of these nitrogen sources showed little or no reactivity.
24. See the Supporting Information for expanded transition-state analysis, HFLC traces, ee analysis, crystal structure data, and assignment of the relative and absolute stereochemistry of the products.
25. Lee, K. Y.; Lee, C. G.; Kim, J. N. Tetrahedron Lett. 2003, 44, 1231-1234.