The intramolecular allenolate rauhut-currier reaction

Journal of Organic Chemistry

Volumn 77, Issue 17, 2012, Pages 7768-7774

  MacKay, James A ^a   Landis, Zachary C ^a   Motika, Stephen E ^a   Kench, Margaret H ^a  

^a ELIZABETHTOWN COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6-MEMBERED RINGS; ALKYNOATES; ALKYNYLS; C-C BONDS; FUNCTIONALIZED; REACTION YIELDS; TO EFFECT;

CHEMISTRY; ORGANIC COMPOUNDS;

ACETYLENE;

ALKYL GROUP; ALKYNE DERIVATIVE; ALLENE DERIVATIVE; CARBON; ELECTROPHILE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; ELECTROPHILICITY; ENANTIOSELECTIVITY; INTRAMOLECULAR ALLENOLATE RAUHUT CURRIER REACTION; REACTION ANALYSIS; SYNTHESIS;

ALKYNES; CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; NITRILES; PHOSPHINES; STEREOISOMERISM;

EID: 84866073366     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3015769     Document Type: Article

References (42)

1. Aroyan, C. E.; Dermenci, A.; Miller, S. J. Tetrahedron 2009, 65, 4069
2. Methot, J. L.; Roush, W. R. Adv. Synth. Catal. 2004, 346, 1035
3. Wang, L. C.; Luis, A. L.; Agaplou, K.; Jang, H. Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402
4. Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404
5. Aroyan, C. E.; Dermenci, A.; Miller, S. J. J. Org. Chem. 2010, 75, 5784
6. Aroyan, C. E.; Miller, S. J. J. Am. Chem. Soc. 2007, 129, 256
7. Wang, J.; Xie, H.; Li, H.; Zu, L.; Wang, W. Angew. Chem., Int. Ed. 2008, 47, 4177
8. Marques-Lopez, E.; Herrera, R. P.; Marks, T.; Jacobs, W. C.; Konning, D.; de Figueiredo, R. M.; Christmann, M. Org. Lett. 2009, 11, 4116
9. Selig, P. S.; Miller, S. J. Tetrahedron Lett. 2011, 52, 2148
10. Wang, X.-F.; Peng, L.; An, J.; Li, C.; Yang, Q.-Q.; Lu, L.-Q.; Gu, F.-L.; Xiao, W.-J. Chem. - Eur. J. 2011, 17, 6484
11. Jellerichs, B. G.; Kong, J.-R.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 7758
12. Luis, A. L.; Krische, M. J. Synthesis 2004, 2579
13. Krafft, M. E.; Haxell, T. F. N. J. Am. Chem. Soc. 2005, 127, 10168
14. Krafft, M. E.; Seibert, K. A.; Haxell, T. F. N.; Hirosawa, C. Chem. Commun. 2005, 5772
15. Krafft, M. E.; Seibert, K. A. Synlett 2006, 3334
16. Krafft, M. E.; Wright, J. A. Chem. Commun. 2006, 2977
17. Thalji, R. K.; Roush, W. R. J. Am. Chem. Soc. 2005, 127, 16778
18. Jin, Z.; Yang, R.; Du, Y.; Tiwari, B.; Ganguly, R.; Chi, Y. R. Org. Lett. 2012, 14, 3226
19. Seidel, F.; Gladysz, J. A. Synlett 2007, 986
20. Dermenci, A.; Selig, P. S.; Domaoal, R. A.; Spasov, K. A.; Anderson, K. S.; Miller, S. J. Chem. Sci. 2011, 2, 1568
21. Gong, J.-J.; Li, T.-Z.; Pan, K.; Wu, X.-Y. Chem. Commun. 2011, 47, 1491
22. Takizawa, S.; Nguyen, T. M.-N.; Grossmann, A.; Enders, D.; Sasai, H. Angew. Chem., Int. Ed. 2012, 51, 5423
23. Ergüden, J.-K.; Moore, H. W. Org. Lett. 1999, 1, 375
24. Agapiou, K.; Krische, M. J. Org. Lett. 2003, 5, 1737
25. Mergott, D. J.; Frank, S. A.; Roush, W. R. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 11955
26. Winbush, S. M.; Mergott, D. J.; Roush, W. R. J. Org. Chem. 2008, 73, 1818
27. Methot, J. L.; Roush, W. R. Org. Lett. 2003, 5, 4223
28. Stark, L. M.; Pekari, K.; Sorensen, E. J. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 12064
29. Webber, P.; Krische, M. J. J. Org. Chem. 2008, 73, 9379
30. Wang, J.-C.; Krische, M. J. Angew. Chem., Int. Ed. 2003, 42, 5855
31. Wang, J.-C.; Ng, S.-S.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 3682
32. Inanaga, J.; Baba, Y.; Hanamoto, T. Chem. Lett. 1993, 2, 241
33. Stewart, I. C.; Bergman, R. G.; Toste, F. D. J. Am. Chem. Soc. 2003, 125, 8696
34. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224
35. Wei, Y.; Sastry, G. N.; Zipse, H. J. Am. Chem. Soc. 2008, 130, 3473
36. Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 2003, 125, 4166
37. Many transition metal catalyzed cycloisomerizations of enynes afford highly enantioenriched products. See: Marinetti, A.; Jullien, H.; Voituriez, A. Chem. Soc. Rev. 2012, 41, 4884 and references cited therein
38. Rank, E.; Bruckner, R. Eur. J. Org. Chem. 1998, 1045
39. Marino, J. P.; Nguyen, H. N. J. Org. Chem. 2002, 67, 6291
40. Magnus, P.; Principe, L. M.; Slater, M. J. J. Org. Chem. 1987, 52, 1483
41. Kabanyane, S. T.; Magee, D. I. Can. J. Chem. 1992, 70, 2758
42. Komeyama, K.; Takahashi, K.; Takaki, K. Org. Lett. 2008, 10, 5119