Synthesis of the first chiral, functionalised-bridged resorcinarenes in asymmetric catalysis: Evidence for intracavity asymmetric catalysis

被引:28
作者
Arnott, G
Heaney, H
Hunter, R [1 ]
Page, PCB
机构
[1] Univ Cape Town, Dept Chem, ZA-7701 Rondebosch, South Africa
[2] Loughborough Univ Technol, Dept Chem, Loughborough LE11 3TU, Leics, England
关键词
bridged resorcinarenes; chiral resorcinarenes; diethylzinc addition; asymmetric catalysis; intracavity catalysis;
D O I
10.1002/ejoc.200400615
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Methodology is presented for synthesis of the first examples of chiral, bridged resorcinarenes with functionality in the bridge as possible sites for intracavity asymmetric catalysis. A preliminary study comparing unfunctionalised with functionalised lines using the enantio selective addition of diethylzinc to benzaldehyde as a probe reaction, provides compelling evidence for intracavity catalysis. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).
引用
收藏
页码:5126 / 5134
页数:9
相关论文
共 42 条
[21]  
Morikawa O, 2000, SYNTHESIS-STUTTGART, P233
[22]   Recent progress in the design and synthesis of artificial enzymes [J].
Motherwell, WB ;
Bingham, MJ ;
Six, Y .
TETRAHEDRON, 2001, 57 (22) :4663-4686
[23]   Increased enantioselectivity in the addition of diethylzinc to benzaldehyde by the use of chiral ligands containing the α-phenylethylamino group in combination with achiral ligands [J].
Muñoz-Muñiz, O ;
Juaristi, E .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (10) :3781-3785
[24]   SYNTHESIS OF (2R,6R)-(-)-2,6-LUPETIDINE - 2,6-DISUBSTITUTED PIPERIDINES AS POTENTIALLY USEFUL C2-SYMMETRIC CHIRAL REAGENTS [J].
NAJDI, S ;
KURTH, MJ .
TETRAHEDRON LETTERS, 1990, 31 (23) :3279-3282
[25]   ENANTIOSELECTIVE ALKYLATION OF CARBONYL-COMPOUNDS - FROM STOICHIOMETRIC TO CATALYTIC ASYMMETRIC INDUCTION [J].
NOYORI, R ;
SUGA, S ;
KAWAI, K ;
OKADA, S ;
KITAMURA, M .
PURE AND APPLIED CHEMISTRY, 1988, 60 (11) :1597-1606
[26]   A practical o-hydroxybenzylamines promoted enantioselective addition of dialkylzincs to aldehydes with asymmetric amplification [J].
Palmieri, G .
TETRAHEDRON-ASYMMETRY, 2000, 11 (16) :3361-3373
[27]   Inherently chiral calix[4]crown ethers [J].
Pappalardo, S ;
Parisi, MF .
TETRAHEDRON LETTERS, 1996, 37 (09) :1493-1496
[28]   Calix[4]arene based monophosphites, identification of three conformations and their use in the rhodium-catalysed hydroformylation of 1-octene [J].
Parlevliet, FJ ;
Kiener, C ;
Fraanje, J ;
Goubitz, K ;
Lutz, M ;
Spek, AL ;
Kamer, PCJ ;
van Leeuwen, PWNM .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2000, (07) :1113-1122
[29]   Asymmetric alkynylzinc additions to aldehydes and ketones [J].
Pu, L .
TETRAHEDRON, 2003, 59 (50) :9873-9886
[30]   Catalytic asymmetric organozinc additions to carbonyl compounds [J].
Pu, L ;
Yu, HB .
CHEMICAL REVIEWS, 2001, 101 (03) :757-824