Alkylidenesilacyclopropanes derived from allenes: Applications to the selective synthesis of triols and homoallylic alcohols

Organic Letters

Volumn 11, Issue 10, 2009, Pages 2173-2175

  Buchner, Kay M ^a   Clark, Timothy B ^a   Loy, Janice M N ^a   Nguyen, Thong X ^a   Woerpel, K A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKADIENE; ALLENE; CYCLOPROPANE DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALCOHOLS; ALKADIENES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLOPROPANES; MOLECULAR STRUCTURE; SILANES; STEREOISOMERISM;

EID: 66149145435     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900456v     Document Type: Article

References (29)

1. Nishina, N.; Yamamoto, Y. Angew. Chem. Int. Ed. 2006, 45, 3314-3317.
2. (a) Ng, S.-S.; Jamison, T. F. J. Am. Chem. Soc. 2005, 127, 7320-7321.
3. (b) Ng, S.-S.; Jamison, T. F. Tetrahedron 2005, 61, 11405-11417.
4. Brammond, K. M.; Kerekes, A. D.; Wan, H. J. Org. Chem. 2002, 67, 5156-5163.
5. Ma, S.; Yu, F.; Gao, W. J. Org. Chem. 2003, 68, 5943-5949.
6. Brandi, A.; Goti, A. Chem. Rev. 1998, 98, 589-635.
7. Shipman, M. Synlett 2006, 3205-3217.
8. Seyferth, D. J. Orsanomet. Chem. 1975, 100, 237-256.
9. (a) Ando, W.; Saso, H. Tetrahedron Lett. 1986, 27, 5625-5628.
10. (b) Saso, H.; Ando, W.; Ueno, K. Tetrahedron 1989, 45, 1929-1940.
11. (a) Driver, T. G.; Woerpel, K. A. J. Am. Chem. Soc. 2003, 125, 10659-10663.
12. (b) Cirakovic, J.; Driver, T. G.; Woerpel, K. A. J. Org. Chem 2004, 69, 4007-4012.
13. (c) Clark, T. B.; Woerpel, K. A. J. Am. Chem. Soc. 2004, 126, 9522-9523.
14. (a) Marshall, J. A.; Ellis, K. C. Org. Lett. 2003, 5, 1729-1732.
15. (b) O'Neil, G. W.; Phillips, A. J. J. Am. Chem. Soc. 2006, 128, 5340-5341.
16. (c) Someya, H.; Kondoh, A.; Sato, A.; Ohmiya, H.; Yorimitsu, H.; Oshima, K. Synlett 2006, 3061-3064.
17. (d) Robertson, J.; Middleton, D. S.; O'Connor, G.; Sardharwala, T. Tetrahedron Lett. 1998, 39, 669-672.
18. (e) Robertson, J.; O'Connor, G.; Sardharwala, T.; Middleton, D. S. Tetrahedron 2000, 56, 8309-8320.
19. (f) Leighton, J. L.; Chapman, E. J. Am. Chem. Soc. 1997, 119, 12416-12417.
20. (g) Hale, M. R.; Hoveyda, A. H. J. Org. Chem. 1992, 57, 1643-1645.
21. Clark, T. B.; Woerpel, K. A. Org. Lett. 2006, 8, 4109-4112.
22. More information is provided as Supporting Information.
23. It is not clear how copper salts catalyze carbonyl insertion. The mechanism of this reaction is currently being investigated.
24. The relative stereochemistry of 10 was determined by X-ray crystallography.
25. Myers, A. G.; Zheng, B. J. Am. Chem. Soc. 1996, 118, 4492-4493.
26. Absolute stereochemistry was determined by X-ray crystallographic analysis of a chiral carbamate derivative. Details are provided as Supporting Information.
27. (a) McNulty, J.; Nair, J. J.; Sliwinski, M.; Harrington, L. E.; Pandey, S. Eur. J. Org. Chem. 2007, 5669-5673.
28. (b) Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392-393.
29. (c) Abiko, A. Acc. Chem. Res. 2004, 37, 387-395.