Development of diamidophosphite ligands and their application to the palladium-catalyzed vinyl-substituted trimethylenemethane asymmetric [3 + 2] cycloaddition

Journal of the American Chemical Society

Volumn 134, Issue 28, 2012, Pages 11319-11321

  Trost, Barry M ^a   Lam, Tom M ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREO- AND ENANTIOSELECTIVITY; HIGH YIELD; PALLADIUM-CATALYZED; STEREOCENTERS; TRIMETHYLENEMETHANE;

CATALYSIS;

LIGANDS;

1,2 DIAMINOCYCLOHEXANE; ALCOHOL DERIVATIVE; ALKANE DERIVATIVE; CYCLOPENTANE; LIGAND; PALLADIUM; PHOSPHITE; VINYL DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CONTROLLED STUDY; CYCLOADDITION; DIASTEREOISOMER; ENANTIOSELECTIVITY; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 84863919346     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja305717r     Document Type: Article

References (26)

1. Trost, B. M. Pure Appl. Chem. 1988, 60, 1615
2. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49
3. Chan, D. M. T. Recent Advances in Palladium-Catalyzed Cycloadditions Involving Trimethylenemethane and its Analogs. In Cycloaddition Reactions in Organic Synthesis, 1 st ed.; Kobayashi, S.; Jorgensen, K. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; pp 57-83.
4. Trost, B. M.; Stambuli, J. P.; Silverman, S. M.; Schwörer, U. J. Am. Chem. Soc. 2006, 128, 13328
5. Trost, B. M.; Bringley, D. A.; Seng, P. S. Org. Lett. 2012, 14, 234
6. Trost, B. M.; Bringley, D. A.; Silverman, S. M. J. Am. Chem. Soc. 2011, 133, 7664
7. Trost., B. M.; Silverman, S. M.; Stambuli, J. P. J. Am. Chem. Soc. 2007, 129, 12398
8. Trost, B. M.; Silverman, S. M. J. Am. Chem. Soc. 2010, 132, 8238
9. Trost, B. M.; Silverman, S. M. J. Am. Chem. Soc. 2012, 134, 4941
10. Das, S.; Chandrasekhar, S.; Yadav, J. S.; Grée, R. Chem. Rev. 2007, 107, 3286
11. Mehta, G.; Srikrishna, A. Chem. Rev. 1997, 97, 671
12. Trost, B. M.; Nanninga, T. N.; Satoh, T. J. Am. Chem. Soc. 1985, 107, 721
13. Trost, B. M.; Cramer, N.; Silverman, S. M. J. Am. Chem. Soc. 2007, 129, 12396
14. Trost, B. M.; Silverman, S. M.; Stambuli, J. P. J. Am. Chem. Soc. 2011, 133, 19483
15. Evans, D. A.; Fandrick, K. R.; Song, H.-J.; Scheidt, K. A.; Xu, R. J. Am. Chem. Soc. 2007, 129, 10029
16. Evans, D. A.; Fandrick, K. R. Org. Lett. 2006, 8, 2249-2252
17. Trost, B. M.; Lehr, K.; Michaelis, D. J.; Xu, J.; Buckl, A. J. Am. Chem. Soc. 2010, 132, 8915
18. See Ayora, I.; Ceder, R. M.; Espinel, M.; Muller, G.; Rocamora, M.; Serrano, M. Organometallics 2011, 30, 115 and references therein
19. Delapierre, G.; Brunel, J. M.; Constantieux, T.; Buono, G. Tetrahedron:Asymmetry 2001, 12, 1345
20. Tsarev, V. N.; Lyubimov, S. E.; Shiryaev, A. A.; Zheglov, S. V.; Bondarev, O. G.; Davankov, V. A.; Kabro, A. A.; Moiseev, S. K.; Kalinin, V. N.; Gavrilov, K. N. Eur. J. Org. Chem. 2004, 2214
21. Hilgraf, R.; Pfaltz, A. Adv. Synth. Catal. 2005, 347, 61
22. Markert, C.; Rösel, P.; Pfaltz, A. J. Am. Chem. Soc. 2008, 130, 3234
23. Gavrilov, K. N.; Zheglov, S. V.; Rastorguev, E. A.; Groshkin, N. N.; Maksimova, M. G.; Benetsky, E. B.; Davankov, V. A.; Reetz, M. T. Adv. Synth. Catal. 2010, 352, 2599
24. Aoyama, H.; Tokunaga, M.; Kiyosu, J.; Iwasawa, T.; Obora, Y.; Tsuji, Y. J. Am. Chem. Soc. 2005, 127, 10474
25. See Mori, M. Adv. Synth. Catal. 2007, 349, 121 and references therein
26. Li, C.-S.; Di, Y.-T.; Mu, S.-Z.; He, H.-P.; Zhang, Q.; Fang, X.; Zhang, Y.; Li, S.-L.; Lu, Y.; Gong, Y.-Q.; Hao, X.-J. J. Nat. Prod. 2008, 71, 1202