Organocatalytic asymmetric hydrophosphination of α,β-Unsaturated aldehydes

被引:151
作者
Carlone, Armando [1 ]
Bartoli, Giuseppe [1 ]
Bosco, Marcella [1 ]
Sambri, Letizia [1 ]
Melchiorre, Paolo [1 ]
机构
[1] Univ Bologna, Dept Organ Chem A Mangini Alma Mater Studiorum, I-40136 Bologna, Italy
关键词
aldehydes; asymmetric synthesis; conjugate addition; organocatalysis; phosphanes;
D O I
10.1002/anie.200700754
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Getting round the (periodic) table: A highly chemo- and enantioselective conjugate addition of diphenylphosphine to α,β-unsaturated aldehydes in the presence of a chiral secondary amine C provides a direct route to chiral β-phosphino aldehyde intermediates (see scheme, TMS = trimethylsilyl). The synthetic utility of the strategy was exemplified in a rapid one-pot (two-step) synthesis of highly enantioenriched 3-amino-phosphines. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4504 / 4506
页数:3
相关论文
共 67 条
[1]   Organocatalytic asymmetric hydrophosphination of nitroalkenes [J].
Bartoli, Giuseppe ;
Bosco, Marcella ;
Carlone, Armando ;
Locatelli, Manuela ;
Mazzanti, Andrea ;
Sambri, Letizia ;
Melchiorre, Paolo .
CHEMICAL COMMUNICATIONS, 2007, (07) :722-724
[2]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[3]   Organocatalytic asymmetric α-bromination of aldehydes and ketones [J].
Bertelsen, S ;
Halland, N ;
Bachmann, S ;
Marigo, M ;
Braunton, A ;
Jorgensen, KA .
CHEMICAL COMMUNICATIONS, 2005, (38) :4821-4823
[4]   Dienamine catalysis:: Organocatalytic asymmetric γ-amination of α,β unsaturated aldehydes [J].
Bertelsen, Slren ;
Marigo, Mauro ;
Brandes, Sebastian ;
Diner, Peter ;
Jorgensen, Karl Anker .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12973-12980
[5]   Asymmetric organocatalytic β-hydroxylation of α,β-unsaturated aldehydes [J].
Bertelsen, Soren ;
Diner, Peter ;
Johansen, Rasmus Lyng ;
Jorgensen, Karl Anker .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (06) :1536-+
[6]  
Blaser H.U., 2004, ASYMMETRIC CATALYSIS
[7]   Direct catalytic enantioselective α-aminoxylation of ketones:: A stereoselective synthesis of α-hydroxy and α,α′-dihydroxy ketones [J].
Bogevig, A ;
Sundén, H ;
Córdova, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (09) :1109-1112
[8]  
Bogevig A, 2002, ANGEW CHEM INT EDIT, V41, P1790, DOI 10.1002/1521-3773(20020517)41:10<1790::AID-ANIE1790>3.0.CO
[9]  
2-Y
[10]  
Bogevig A., 2002, ANGEW CHEM, V114, P1868