Citation:
Barbara Villa-Marcos, Jianliang Xiao. Barbara Villa-Marcos, Jianliang Xiao[J]. Chinese Journal of Catalysis,
;2015, 36(1): 106-112.
doi:
10.1016/S1872-2067(14)60246-1
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A new protocol that enables asymmetric hydroaminomethylation of styrenes to afford chiral amines has been developed. Catalysed by an Rh-phosphine species and a chiral phosphoric acid, styrenes are converted into β-chiral amines with good enantioselectivities under syngas in the presence of an amine and Hantzsch ester. The reaction involves two key steps, hydroformylation and reductive amination, with the former catalysed by the Rh species whilst the latter by the phosphoric acid.
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[1]
[1] Li C Q, Wang C, Villa-Marcos B, Xiao J L. J Am Chem Soc, 2008, 130: 14450
-
[2]
[2] Li C Q, Villa-Marcos B, Xiao J L. J Am Chem Soc, 2009, 131: 6967
-
[3]
[3] Villa-Marcos B, Li C Q, Mulholland K R, Hogan P J, Xiao J L. Molecules, 2010, 15: 2453
-
[4]
[4] Tang WJ, Johnston S, Iggo J A, Berry N G, Phelan M, Lian L Y, Bacsa J, Xiao J L. Angew Chem Int Ed, 2013, 52: 1668
-
[5]
[5] Tang W J, Johnston S, Li C Q, Iggo J A, Bacsa J, Xiao J L. Chem Eur J, 2013, 19: 14187
-
[6]
[6] Van Leeuwen P W N M, Claver C. Rhodium Catalyzed Hydroformylation. Netherlands: Springer, 2000
-
[7]
[7] Marcelli T, Hammar P, Himo F. Adv Synth Catal, 2009, 351: 525
-
[8]
[8] Eilbracht P, Barfacker L, Buss C, Hollmann C, Kitsos-Rzychon B E, Kranemann C L, Rische T, Roggenbuck R, Schmidt A. Chem Rev, 1999, 99: 3329
-
[9]
[9] Ahmed M, Seayad A M, Jackstel R, Beller M. J Am Chem Soc, 2003, 125: 10311
-
[10]
[10] Reppe W, Vetter H. Liebigs Ann Chem, 1953, 582: 133
-
[11]
[11] Crozet D, Urrutigoity M, Kalck P. ChemCatChem, 2011, 3: 1102
-
[12]
[12] Wu L P, Fleischer I, Jackstell R, Beller M. J Am Chem Soc, 2013, 135: 3989
-
[13]
[13] Gülak S, Wu L P, Liu Q, Franke R, Jackstell R, Beller M. Angew Chem Int Ed, 2014, 53: 7320
-
[14]
[14] Crozet D, Kefalidis C E, Urrutigoïty M, Maron L, Kalck P. ACS Catal, 2014, 4: 435
-
[15]
[15] Noonan G M, Newton D, Cobley C J, Suárez A, Pizzano A, Clarke M L. Adv Synth Catal, 2010, 352: 1047
-
[16]
[16] Guo Y, Fu H Y, Chen H, Li X J. Catal Commum, 2008, 9: 1842
-
[17]
[17] Hoffmann S, Nicoletti M, List B. J Am Chem Soc, 2006, 128: 13074
-
[18]
[18] Moser W R, Papile C J, Brannon D A, Duwell R A, Weininger S J. J Mol Catal, 1987, 41: 271
-
[19]
[19] Mrsic N, Minnaard A J, Feringa B L, de Vries J G. J Am Chem Soc, 2009, 131: 8358
-
[20]
[20] Rubio-Pérez L, Pérez-Flores F J, Sharma P, Velasco L, Cabrera A. Org Lett, 2009, 11: 265
-
[21]
[21] Hoffmann S, Seayad A M, List B. Angew Chem Int Ed, 2005, 44: 7424
-
[22]
[22] Storer R I, Carrera D E, Ni Y, MacMillan D W C. J Am Chem Soc, 2006, 128: 84
-
[23]
[23] Yu S C, Chie Y M, Guan Z H, Zou Y P, Li W, Zhang X. Org Lett, 2009, 11: 241
-
[24]
[24] Van Leeuwen P W N M, Kamer P C J, Reek J N H, Dierkes P. Chem Rev, 2000, 100: 2741
-
[25]
[25] Wang C, Pettman A, Basca J, Xiao J L. Angew Chem Int Ed, 2010, 49: 7548
-
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