Synthesis and application in asymmetric C-C bond formation of solution phase ligand libraries of monodentate phosphoramidites

被引:32
作者
Duursma, A
Lefort, L
Boogers, JAF
de Vries, AHM
de Vries, JG
Minnaard, AJ
Feringa, BL
机构
[1] Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands
[2] DSM Pharma Chem Adv Synth Catalysis & Dev, NL-6160 MD Geleen, Netherlands
关键词
D O I
10.1039/b404996a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A library of 96 unique monodentate phosphoramidite ligands has been synthesized in solution and used in the asymmetric conjugate addition of potassium vinyltrifluoroborate to enones resulting in up to 88% ee.
引用
收藏
页码:1682 / 1684
页数:3
相关论文
共 24 条
[1]   Partially hydrogenated 1,1′-binaphthyl as ligand scaffold in metal-catalyzed asymmetric synthesis [J].
Au-Yeung, TTL ;
Chan, SS ;
Chan, ASC .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (05) :537-555
[2]   High efficiency and enantioselectivity in the Rh-catalyzed conjugate addition of arylboronic acids using monodentate phosphoramidites [J].
Boiteau, JG ;
Minnaard, AJ ;
Feringa, BL .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (24) :9481-9484
[3]   Rhodium-catalyzed asymmetric conjugate additions of boronic acids using monodentate phosphoramidite ligands [J].
Boiteau, JG ;
Imbos, F ;
Minnaard, AJ ;
Feringa, BL .
ORGANIC LETTERS, 2003, 5 (05) :681-684
[4]   Rhodium-catalyzed asymmetric conjugate additions of boronic acids using monodentate phosphoramidite ligands (vol 5, pg 682, 2003) [J].
Boiteau, JG ;
Imbos, R ;
Minnaard, AJ ;
Feringa, BL .
ORGANIC LETTERS, 2003, 5 (08) :1385-1385
[5]  
COFFEN DL, 2002, HDB COMBINATORIAL CH, V1, P10
[6]  
de Vries JG, 2003, EUR J ORG CHEM, V2003, P799
[7]   Polymer-supported phosphoramidites:: highly efficient and recyclable catalysts for asymmetric hydrogenation of dimethylitaconate and dehydroamino acids and esters [J].
Doherty, S ;
Robins, EG ;
Pál, I ;
Newman, CR ;
Hardacre, C ;
Rooney, D ;
Mooney, DA .
TETRAHEDRON-ASYMMETRY, 2003, 14 (11) :1517-1527
[8]   First examples of improved catalytic asymmetric C-C bond formation using the monodentate ligand combination approach [J].
Duursma, A ;
Hoen, R ;
Schuppan, J ;
Hulst, R ;
Minnaard, AJ ;
Feringa, BL .
ORGANIC LETTERS, 2003, 5 (17) :3111-3113
[9]   One-pot multi-substrate enantioselective conjugate addition of diethylzinc to nitroalkenes [J].
Duursma, A ;
Minnaard, AJ ;
Feringa, BL .
TETRAHEDRON, 2002, 58 (29) :5773-5778
[10]   Combinatorial libraries of chiral ligands for enantioselective catalysis [J].
Gennari, C ;
Piarulli, U .
CHEMICAL REVIEWS, 2003, 103 (08) :3071-3100