Polymer supported trans-1-phenylsulfonylamino-2-isoborneolsulfonylaminocyclohexane ligand for the titanium catalyzed organozinc addition to ketones

被引：33
作者：
Forrat, Vicente J. [1 ]
Ramon, Diego J. [1 ]
Yus, Miguel [1 ]
机构：
[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, Inst Sintesis Organ, E-03080 Alicante, Spain
来源：
TETRAHEDRON-ASYMMETRY | 2006年 / 17卷 / 14期
关键词：
D O I：
10.1016/j.tetasy.2006.07.038
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The catalytic enantioselective addition of different organozinc reagents, such as diethylzinc, or in situ generated phenylzinc derivatives to simple ketones was accomplished using titanium tetraisopropoxide and supported chiral ligands derived from trans-1-phenylsulfonylamino-2-isoborneolsulfonylamidocyclohexane, to give the corresponding tertiary alcohols with enantioselectivities up to > 99%. A simple and efficient procedure for the synthesis of the disulfonamide monomeric ligand and the corresponding polymerization is described. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2054 / 2058
页数：5
相关论文
共 82 条
[1]   The NiCl2-Li-arene (cat.) combination as reducing system, part 9:: Catalytic hydrogenation of organic compounds using the NiCl2-Li-(Naphthalene or polymer-supported naphthalene) (cat.) combination [J].
Alonso, F ;
Candela, P ;
Gómez, C ;
Yus, M .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) :275-279
[2]  
Altava B, 2000, ANGEW CHEM INT EDIT, V39, P1503, DOI 10.1002/(SICI)1521-3773(20000417)39:8<1503::AID-ANIE1503>3.0.CO
[3]  
2-B
[4]  
BAGANZ H, 1957, Arch Pharm Ber Dtsch Pharm Ges, V290/62, P567, DOI 10.1002/ardp.19572901109
[5]   Synthesis of new chiral hydroxy oxazolines and their use in the catalytic asymmetric phenyl transfer to aldehydes [J].
Bolm, C ;
Schmidt, F ;
Zani, L .
TETRAHEDRON-ASYMMETRY, 2005, 16 (07) :1367-1376
[6]   New chiral ligands derived from mandelic acid: Synthesis and application in the asymmetric phenyl transfer reaction to an aromatic aldehyde [J].
Bolm, C ;
Zani, L ;
Rudolph, J ;
Schiffers, I .
SYNTHESIS-STUTTGART, 2004, (13) :2173-2180
[7]  
Bolm C, 2001, ANGEW CHEM INT EDIT, V40, P3285
[8]   Synthesis of resins with pendently-bound chiral manganese-salen complexes and use as heterogeneous asymmetric alkene epoxidation catalysts [J].
Canali, L ;
Sherrington, DC ;
Deleuze, H .
REACTIVE & FUNCTIONAL POLYMERS, 1999, 40 (02) :155-168
[9]   Lithiation reactions catalyzed by linear and cross-linked arene-based polymers.: Generation of functionalized organolithium compounds [J].
Candela, P ;
Gómez, C ;
Yus, M .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 40 (06) :795-801
[10]  
Christoffers J, 2005, QUATERNARY STEREOCENTERS: CHALLENGES AND SOLUTIONS FOR ORGANIC SYNTHESIS, P1, DOI 10.1002/3527606858
123456789