Switch in stereoselectivity caused by the isocyanide structure in the rhodium-catalyzed silylimination of alkynes

Journal of the American Chemical Society

Volumn 133, Issue 26, 2011, Pages 10014-10017

  Fukumoto, Yoshiya ^a   Hagihara, Motoyuki ^a   Kinashi, Fuyuko ^a   Chatani, Naoto ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL ISOCYANIDES; E-ISOMERS; GOOD YIELD; HYDROSILANES; ISOCYANIDES; RHODIUM-CATALYZED; TERMINAL ALKYNE; UNSATURATED IMINES;

ACETYLENE; ISOMERS; RHODIUM;

CYANIDES;

ALKYNE DERIVATIVE; CYANIDE; HYDROSILANE; IMINE; ISOCYANIDE; RHODIUM; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMER; SILYLIMINATION; STEREOCHEMISTRY;

EID: 79959891564     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja202881y     Document Type: Article

References (34)

1. For reviews, see: Curtis-Long, M. J.; Aye, Y. Chem. - Eur. J. 2009, 15, 5402-5416
2. Oshima, K. Sci. Synth. 2002, 4, 713-756
3. Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063-2192
4. Fleming, I.; Dunogùs, J.; Smithers, R. Org. React. 1989, 37, 57-575
5. For recent reviews, see: Denmark, S. E. J. Org. Chem. 2009, 74, 2915-2927
6. Denmark, S. E.; Regens, C. S. Acc. Chem. Res. 2008, 41, 1486-1499
7. Denmark, S. E.; Baird, J. D. Chem. - Eur. J. 2006, 12, 4954-4963
8. Hiyama, T.; Shirakawa, E. Top. Curr. Chem. 2002, 219, 61-85
9. For general reviews, see: Suginome, M.; Matsuda, T.; Ohmura, T.; Seki, A.; Murakami, M. In Comprehensive Organometallic Chemistry III; Crabtree, R. H.; Mingos, M. P., Eds.; Elsevier: Amsterdam, 2007; Vol. 10, Chapter 16, pp 725-787.
10. Beletskaya, I.; Moberg, C. Chem. Rev. 2006, 106, 2320-2354
11. Suginome, M.; Ito, Y. Chem. Rev. 2000, 100, 3221-3256
12. Beletskaya, I.; Moberg, C. Chem. Rev. 1999, 99, 3435-3461
13. For recent reviews, see: Ball, Z. T. In Comprehensive Organometallic Chemistry III; Crabtree, R. H.; Mingos, M. P., Eds.; Elsevier: Amsterdam, 2007; Vol. 10, Chapter 17, pp 789-813.
14. Trost, B. M.; Ball, Z. T. Synthesis 2005, 853-887
15. Yoshikawa, E.; Kasahara, M.; Asao, N.; Yamamoto, Y. Tetrahedron Lett. 2000, 41, 4499-4502
16. Yoshikawa, E.; Gevorgyan, V.; Asao, N.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 6781-6786
17. Asao, N.; Yoshikawa, E.; Yamamoto, Y. J. Org. Chem. 1996, 61, 4874-4875
18. Yeon, S. H.; Han, J. S.; Hong, E.; Do, Y.; Jung, I. N. J. Organomet. Chem. 1995, 499, 159-165 For a review, see: Asao, N.; Yamamoto, Y. Bull. Chem. Soc. Jpn. 2000, 73, 1071-1087
19. For preceding studies, see: Ojima, I.; Ingallina, P.; Donovan, R. J.; Clos, N. Organometallics 1991, 10, 38-41
20. Matsuda, I.; Ogiso, A.; Sato, S.; Izumi, Y. J. Am. Chem. Soc. 1989, 111, 2332-2333 For a review, see: Aronica, L. A.; Caporusso, A. M.; Salvadori, P. Eur. J. Org. Chem. 2008, 3039-3060
21. For recent reports on imine syntheses using isocyanide as a C1 source, see: Tobisu, M.; Imoto, S.; Ito, S.; Chatani, N. J. Org. Chem. 2010, 75, 4835-4840
22. Park, S.; Shintani, R.; Hayashi, T. Chem. Lett. 2009, 38, 204-205
23. Zhang, W.-X.; Nishiura, M.; Hou, Z. Angew. Chem., Int. Ed. 2008, 47, 9700-9703
24. Barnea, E.; Andrea, T.; Berthet, J.-C.; Ephritikhine, M.; Eisen, M. S. Organometallics 2008, 27, 3103-3112 and references cited therein
25. For example, see: Tobisu, M.; Kitajima, A.; Yoshioka, S.; Hyodo, I.; Oshita, M.; Chatani, N. J. Am. Chem. Soc. 2007, 129, 11431-11437
26. For recent reviews of isocyanides in organic synthesis, see: Lygin, A. V.; de Meijere, A. Angew. Chem., Int. Ed. 2010, 49, 9094-9124
27. El Kaim, L.; Grimaud, L. Tetrahedron 2009, 65, 2153-2171
28. Dömling, A. Chem. Rev. 2006, 106, 17-89
29. Suginome, M.; Ito, Y. Sci. Synth. 2004, 19, 445-530
30. 4. However, no formation of the corresponding imines was described. See: Ojima, I.; Donovan, R. J.; Eguchi, M.; Shay, W. R.; Ingallina, P.; Korda, A.; Zeng, Q. Tetrahedron 1993, 49, 5431-5444
31. Ojima, I.; Clos, N.; Donovan, R. J.; Ingallina, P. Organometallics 1990, 9, 3127-3133
32. Tanke, R. S.; Crabtree, R. H. J. Chem. Soc., Chem. Commun. 1990, 1056-1057
33. Sridevi, V. S.; Fan, W. Y.; Leong, W. K. Organometallics 2007, 26, 1157-1160
34. Many studies have found that a silyl group can slightly stabilize a cation on an α-carbon. For a review, see: Lambert, J. B. Tetrahedron 1990, 46, 2677-2689