Synthesis of a library of chiral α-amino acid-based borate counteranions and their application to copper catalyzed olefin cyclopropanation

被引:36
作者
Llewellyn, DB [1 ]
Arndtsen, BA [1 ]
机构
[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
D O I
10.1016/j.tetasy.2005.04.004
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Twenty borate counteranions have been prepared from tartaric acid and alpha-amino acid derivatives. Ion pairing of these anions to a copper cation can be Used to induce enantioselectivity into the copper catalyzed cyclopropanation of styrene. Structural modification of the anion provides insight into the importance of each component of the counteranion in asymmetric induction. (C) 2005 Published by Elsevier Ltd.
引用
收藏
页码:1789 / 1799
页数:11
相关论文
共 71 条
[1]   Catalytic asymmetric Darzens condensation under phase-transfer-catalyzed conditions [J].
Arai, S ;
Shioiri, T .
TETRAHEDRON LETTERS, 1998, 39 (15) :2145-2148
[2]   Synthesis of macrocyclic polyhydroxy tetralactams derived from L-tartaric acid and beta-hydroxyglutaric acid [J].
Arnaud, N ;
Picard, C ;
Cazaux, L ;
Tisnes, P .
TETRAHEDRON, 1997, 53 (40) :13757-13768
[3]   Cationic acetyl complexes of iron(II) and ruthenium(II) bearing neutral N,O ligands: Synthesis, characterization, and interionic solution structure by NOESY NMR spectroscopy [J].
Bellachioma, G ;
Cardaci, G ;
Gramlich, V ;
Macchioni, A ;
Valentini, M ;
Zuccaccia, C .
ORGANOMETALLICS, 1998, 17 (23) :5025-5030
[4]   Application of H-1-NOESY NMR spectroscopy to the investigation of ion pair solution structures of organometallic complexes by the detection of interionic contacts [J].
Bellachioma, G ;
Cardaci, G ;
Macchioni, A ;
Reichenbach, G ;
Terenzi, S .
ORGANOMETALLICS, 1996, 15 (21) :4349-4351
[5]  
Bodansky M., 1994, PRACTICE PEPTIDE SYN, V2nd
[6]  
Boeseken J, 1925, RECL TRAV CHIM PAY-B, V44, P758
[7]   Asymmetric syntheses of (R)- and (S)-2-aminobutanesulfonic acid and their 3,3-dimethylderivatives [J].
Braghiroli, D ;
DiBella, M .
TETRAHEDRON-ASYMMETRY, 1996, 7 (07) :2145-2150
[8]   Towards phase-transfer catalysts with a chiral anion: inducing asymmetry in the reactions of cations [J].
Carter, C ;
Fletcher, S ;
Nelson, A .
TETRAHEDRON-ASYMMETRY, 2003, 14 (14) :1995-2004
[9]   EFFECT OF CHIRAL QUATERNARY AMMONIUM-SALTS ON (SALEN)MN-CATALYZED EPOXIDATION OF CIS-OLEFINS - A HIGHLY ENANTIOSELECTIVE, CATALYTIC ROUTE TO TRANS-EPOXIDES [J].
CHANG, SB ;
GALVIN, JM ;
JACOBSEN, EN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) :6937-6938
[10]  
Chataigner I, 2000, ANGEW CHEM INT EDIT, V39, P916, DOI 10.1002/(SICI)1521-3773(20000303)39:5<916::AID-ANIE916>3.0.CO