Catalytic enantioselective reduction of β,β-disubstituted vinyl phenyl Sulfones by using bisphosphine monoxide Ligands

被引:138
作者
Desrosiers, Jean-Nicolas [1 ]
Charette, Andre B. [1 ]
机构
[1] Univ Montreal, Dept Chim, Montreal, PQ H3S 3J7, Canada
关键词
asymmetric catalysis; copper; phosphine ligands; reduction; sulfones;
D O I
10.1002/anie.200701367
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Synthesis of chiral sulfones: A copper-phosphine complex efficiently provided optically active alkyl phenyl sulfones by hydrosilylation at room temperature. The reduction of β,β-disubstituted vinyl sulfones in the presence of the Me-DuPhos monoxide ligand lead to excellent enantiomeric excesses and high yields (see scheme). The prepared chiral sulfones were desulfonylated and subjected to Julia olefination conditions. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:5955 / 5957
页数:3
相关论文
共 39 条
[11]   Mixed phosphine-phosphine oxide ligands [J].
Grushin, VV .
CHEMICAL REVIEWS, 2004, 104 (03) :1629-1662
[12]   Catalytic enantioselective conjugate reduction of lactones and lactams [J].
Hughes, G ;
Kimura, M ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) :11253-11258
[13]  
JULIA M, 1973, TETRAHEDRON LETT, P4833
[14]  
Kaiser S., 2006, ANGEW CHEM, V118, P5318
[15]   Iridium catalysts with bicyclic pyridine-phosphinite ligands: Asymmetric hydrogenation of olefins and furan derivatives [J].
Kaiser, Stefan ;
Smidt, Sebastian R. ;
Pfaltz, Andreas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (31) :5194-5197
[16]  
Keck G. E., 2001, ANGEW CHEM, V113, P237
[17]  
Keck GE, 2001, ANGEW CHEM INT EDIT, V40, P231, DOI 10.1002/1521-3773(20010105)40:1<231::AID-ANIE231>3.0.CO
[18]  
2-W
[19]  
Kelly S. E., 1991, COMPREHENSIVE ORGANI, V1, P792
[20]  
KOCIENSKI P, 1985, PHOSPHOROUS SULPHUR, V24, P97