Chiral copper(II) bisoxazoline covalently anchored to silica and mesoporous MCM-41 as a heterogeneous catalyst for the enantioselective Friedel-Crafts hydroxyalkylation

被引:129
作者
Corma, A
García, H
Moussaif, A
Sabater, MJ
Zniber, R
Redouane, A
机构
[1] Univ Politecn Valencia, CSIC, Inst Tecnol Quim, Valencia 46022, Spain
[2] Univ Mohammed 5, Fac Sci, Rabat, Morocco
关键词
D O I
10.1039/b200768a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Two solid catalysts in which a chiral copper(II) bisoxazoline has been covalently anchored on silica and MCM-41 have been prepared; the solids are enantioselective catalysts (up to 92% ee) for the Friedel-Crafts hydroxyalkylation of 1,3-dimethoxybenzene with 3,3,3-trifluoropyruvate.
引用
收藏
页码:1058 / 1059
页数:2
相关论文
共 18 条
[1]   Poly(ethylene glycol)-supported bisoxazolines as ligands for catalytic enantioselective synthesis [J].
Annunziata, R ;
Benaglia, M ;
Cinquini, M ;
Cozzi, F ;
Pitillo, M .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (09) :3160-3166
[2]   Bis(oxazoline)copper complexes covalently bonded to insoluble support as catalysts in cyclopropanation reactions [J].
Burguete, MI ;
Fraile, JM ;
García, JI ;
García-Verdugo, E ;
Herrerías, CI ;
Luis, SV ;
Mayoral, JA .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) :8893-8901
[3]   Mesopore immobilised copper bis(oxazoline) complexes for enantioselective catalysis [J].
Clarke, RJ ;
Shannon, IJ .
CHEMICAL COMMUNICATIONS, 2001, (19) :1936-1937
[4]   PREPARATION OF CHIRAL BISOXAZOLINES - OBSERVATIONS ON THE EFFECT OF SUBSTITUENTS [J].
DENMARK, SE ;
NAKAJIMA, N ;
NICAISE, OJC ;
FAUCHER, AM ;
EDWARDS, JP .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) :4884-4892
[5]   C2-symmetric copper(II) complexes as chiral Lewis acids.: Enantioselective catalysis of the glyoxylate-ene reaction [J].
Evans, DA ;
Burgey, CS ;
Paras, NA ;
Vojkovsky, T ;
Tregay, SW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (23) :5824-5825
[6]   Bis(oxazoline)-copper complexes, supported by electrostatic interactions, as heterogeneous catalysts for enantioselective cyclopropanation reactions:: Influence of the anionic support [J].
Fraile, JM ;
García, JI ;
Mayoral, JA ;
Tarnai, T ;
Harmer, MA .
JOURNAL OF CATALYSIS, 1999, 186 (01) :214-221
[7]   Asymmetric palladium-catalyzed allylic alkylation using bis(oxazoline) ligands:: Phenomenal reversal of enantioselectivity with a single chiral backbone [J].
Hoarau, O ;
Aït-Haddou, H ;
Daran, JC ;
Cramailère, D ;
Balavoine, GGA .
ORGANOMETALLICS, 1999, 18 (23) :4718-4723
[8]   The catalytic activity of new chiral salen complexes immobilized on MCM-41 by multi-step grafting in the asymmetric epoxidation [J].
Kim, GJ ;
Shin, JH .
TETRAHEDRON LETTERS, 1999, 40 (37) :6827-6830
[9]   Catalytic asymmetric heterogeneous aziridination of alkenes using zeolite CuHY with [N-(p-tolylsulfonyl)imino]phenyliodinane as nitrene donor [J].
Langham, C ;
Taylor, S ;
Bethell, D ;
McMorn, P ;
Page, PCB ;
Willock, DJ ;
Sly, C ;
Hancock, FE ;
King, F ;
Hutchings, GJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (05) :1043-1049
[10]   Heterogeneous asymmetric Diels-Alder reactions using a copper-chiral bis(oxazoline) complex immobilized on mesoporous silica [J].
Park, JK ;
Kim, SW ;
Hyeon, T ;
Kim, BM .
TETRAHEDRON-ASYMMETRY, 2001, 12 (21) :2931-2935