Polystyrene-supported (R)-2-piperazino-1,1,2-triphenylethanol:: A readily available supported ligand with unparalleled catalytic activity and enantioselectivity

被引：35

作者：

Castellnou, D

Solà, L

Jimeno, C

Fraile, JM

Mayoral, JA

Riera, A

Pericàs, MA

机构：

[1] Univ Barcelona, Dept Quim Inorgan & Parc Cientif, E-08028 Barcelona, Spain

[2] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain

[3] Univ Zaragoza, Inst Ciencia Mat Aragon, CSIC, Zaragoza 50009, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 02期

关键词：

D O I：

10.1021/jo048310d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

DIAGRAM A very active and highly enantioselective catalytic resin, designed for minimal perturbation of the catalytic center by the polymer matrix, has been assembled in two steps from (S)-triphenylethylene oxide, piperazine, and Merrifield resin and tested in the enantioselective ethylation of aldehydes. 1-Arylpropanols of 94-95 % ee are obtained in high yield by the use of only 2 mol % of catalytic resin at 0 degreesC for 4 h.

引用

页码：433 / 438

页数：6

共 20 条

[1] Polymer-supported ferrocenyl oxazolines for the catalyzed highly enantioselective phenyl transfer to aldehydes
Bolm, C
Hermanns, N
Classen, A
Muñiz, K
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (14) : 1795 - 1798
[2] HIGHLY ENANTIOSELECTIVE, CATALYTIC EPOXIDATION OF TRISUBSTITUTED OLEFINS
BRANDES, BD
JACOBSEN, EN
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (16) : 4378 - 4380
[3] Recent advances in asymmetric C-C and C-heteroatom bond forming reactions using polymer-bound catalysts
Bräse, S
Lauterwasser, F
Ziegert, RE
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (08) : 869 - 929
[4] New supported β-amino alcohols as efficient catalysts for the enantioselective addition of diethylzinc to benzaldehyde under flow conditions
Burguete, MI
García-Verdugo, E
Vicent, MJ
Luis, SV
Pennemann, H
von Keyserling, NG
Martens, J
[J]. ORGANIC LETTERS, 2002, 4 (22) : 3947 - 3950
[5] REGIOCHEMICAL CONTROL OF THE RING-OPENING OF 1,2-EPOXIDES BY MEANS OF CHELATING PROCESSES .5. SYNTHESIS AND REACTIONS OF SOME 2,3-EPOXY-1-ALKANOL DERIVATIVES
CHINI, M
CROTTI, P
FLIPPIN, LA
GARDELLI, C
GIOVANI, E
MACCHIA, F
PINESCHI, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) : 1221 - 1227
[6] DEVOS DE, 2000, CHIRAL CATALYSIS IMM
[7] Polymer-supported chiral catalysts with positive support effects
Fan, QH
Wang, R
Chan, ASC
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (14) : 1867 - 1871
[8] 2-piperidino-1,1,2-triphenylethanol:: A highly effective catalyst for the enantioselective arylation of aldehydes
Fontes, M
Verdaguer, X
Solà, L
Pericàs, MA
Riera, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07) : 2532 - 2543
[9] New silica-immobilized chiral amino alcohol for the enantioselective addition of diethylzinc to benzaldehyde
Fraile, JM
Mayoral, JA
Serrano, J
Pericàs, MA
Solà, L
Castellnou, D
[J]. ORGANIC LETTERS, 2003, 5 (23) : 4333 - 4335
[10] Enantioselective addition of dimethylzinc to aldehydes:: assessment of optimal N,N-substitution for 2-dialkylamino-1,1,2-triphenylethanol ligands
García-Delgado, N
Fontes, M
Pericàs, MA
Riera, A
Verdaguer, X
[J]. TETRAHEDRON-ASYMMETRY, 2004, 15 (13) : 2085 - 2090

← 1 2 →