Metallocene sulfoxides as precursors of metallocenes with planar chirality

被引:75
作者
Ferber, Benoit [1 ]
Kagan, Henri B. [1 ]
机构
[1] Univ Paris 11, ICMMO, CNRS, UMR 8182, F-914055 Orsay, France
关键词
chiral ligands; enantioselective catalysis; ferrocenes; lithiation; planar chirality; sulfoxides;
D O I
10.1002/adsc.200600639
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The preparation of metallocene sulfoxides and their ortho-diastereoselective functionalization are described. The applications of enantiopure 1,2- and 1,3-disubstituted metallocenes are reviewed, with special emphasis on the preparation of ligands for asymmetric catalysis. The sulfoxide functionality is a useful, traceless, chiral diastereoselective ortho-directing group, as explained in the article. It allows one to synthesize a wide range of enantiopure metallocenes with planar chirality and predictible configuration. Most of the examples are related to the ferrocene area.
引用
收藏
页码:493 / 507
页数:15
相关论文
共 80 条
[41]   Enantioselective synthesis of sulfur-containing 1,2-disubstituted ferrocenes [J].
Hua, DH ;
Lagneau, NM ;
Chen, Y ;
Robben, PM ;
Clapham, G ;
Robinson, PD .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) :4508-4509
[42]   RACEMIZATION AND CLEAVAGE OF SULFOXIDES BY METHYLLITHIUM [J].
JACOBUS, J ;
MISLOW, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (20) :5228-&
[43]   New air-stable planar chiral ferrocenyl monophosphine ligands: Suzuki cross-coupling of aryl chlorides and bromides [J].
Jensen, JF ;
Johannsen, M .
ORGANIC LETTERS, 2003, 5 (17) :3025-3028
[44]   Modular approach to novel chiral aryl-ferrocenyl phosphines by Suzuki cross-coupling [J].
Jensen, JF ;
Sotofte, I ;
Sorensen, HO ;
Johannsen, M .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (04) :1258-1265
[45]   Towards new ferrocenyl ligands for asymmetric catalysis [J].
Kagan, HB ;
Diter, P ;
Gref, A ;
Guillaneux, D ;
Szymczak, AM ;
Rebiere, F ;
Riant, O ;
Samuel, O ;
Taudien, S .
PURE AND APPLIED CHEMISTRY, 1996, 68 (01) :29-36
[46]  
KATRITZKY AR, 1994, COMPREHENSIVE ORGANI, V4, P958
[47]   Ferrocenyl-QUINAP:: a planar chiral P,N-ligand for palladium-catalyzed allylic substitution reactions [J].
Kloetzing, RJ ;
Knochel, P .
TETRAHEDRON-ASYMMETRY, 2006, 17 (01) :116-123
[48]   Chiral sulfur-containing 1,2-disubstituted ferrocenes [J].
Lagneau, NM ;
Chen, Y ;
Robben, PM ;
Sin, HS ;
Takasu, K ;
Chen, JS ;
Robinson, PD ;
Hua, DH .
TETRAHEDRON, 1998, 54 (26) :7301-7334
[49]   Applications of catalytic asymmetric sulfide oxidations to the syntheses of biologically active sulfoxides [J].
Legros, J ;
Dehli, JR ;
Bolm, C .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (01) :19-31
[50]  
LOCKARD JP, 1973, SYNTHESIS-STUTTGART, P485