Towards phase-transfer catalysts with a chiral anion: inducing asymmetry in the reactions of cations

被引：75

作者：

Carter, C

Fletcher, S

Nelson, A ^{[1
]}

机构：

[1] Univ Leeds, Dept Chem, Leeds LS2 9JT, W Yorkshire, England

[2] Syngenta, Huddersfield HD2 1FF, W Yorkshire, England

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 14期

关键词：

D O I：

10.1016/S0957-4166(03)00367-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The ability of chiral anions, for example bis[1,1'-bi-2-naplitholato]borate, to induce asymmetry in the reactions of prochiral cations was investigated. Ion-pairing of a borate anion with an aziridinium ion was demonstrated by NMR spectroscopy. The addition of N-methyl indole to an iminium ion (benzylidenedimethylammonium) and the ring-opening of all aziridinium ion (1.2-diphenyl-3-azonia-spiro[2.4]heptane) with benzylamine were studied. Low, but significant, (<15%) enantioselectivities were induced in the formation of the diamine benzyl-(1',2'-diphenyl-2-pyrrolidin-1-yl-ethyl)-amine. The counterion of the additive was found to have a remarkable effect on the yield and the sense of enantioselectivity of these reactions. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：1995 / 2004

页数：10

共 40 条

[1] Synthetic approaches to the manumycin A, B and C antibiotics: The first total synthesis of (+)-manumycin A
Alcaraz, L
Macdonald, G
Ragot, J
Lewis, NJ
Taylor, RJK
[J]. TETRAHEDRON, 1999, 55 (12) : 3707 - 3716
[2] The preparation of β-substituted amines from mixtures of epoxide opening products via a common aziridinium ion intermediate
Anderson, SR
Ayers, JT
DeVries, KM
Ito, F
Mendenhall, D
Vanderplas, BC
[J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (14) : 2655 - 2663
[3] Asymmetric cyclopropanation reaction under phase-transfer catalyzed conditions
Arai, S
Nakayama, K
Ishida, T
Shioiri, T
[J]. TETRAHEDRON LETTERS, 1999, 40 (22) : 4215 - 4218
[4] Catalytic asymmetric Darzens condensation under phase-transfer-catalyzed conditions
Arai, S
Shioiri, T
[J]. TETRAHEDRON LETTERS, 1998, 39 (15) : 2145 - 2148
[5] Self-assembly of heterobimetallic complexes and reactive nucleophiles: A general strategy for the activation of asymmetric reactions promoted by heterobimetallic catalysts
Arai, T
Yamada, YMA
Yamamoto, N
Sasai, H
Shibasaki, M
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (11) : 1368 - 1372
[6] Asymmetric PTC C-alkylation mediated by TADDOL -: novel route to enantiomerically enriched α-alkyl-α-amino acids
Belokon, YN
Kochetkov, KA
Churkina, TD
Ikonnikov, NS
Chesnokov, AA
Larionov, OV
Parmár, VS
Kumar, R
Kagan, HB
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (05) : 851 - 857
[7] Chiral salen-metal complexes as novel catalysts for asymmetric phase transfer alkylations
Belokon, YN
North, M
Kublitski, VS
Ikonnikov, NS
Krasik, PE
Maleev, VI
[J]. TETRAHEDRON LETTERS, 1999, 40 (33) : 6105 - 6108
[8] A practical asymmetric synthesis of α-methyl α-amino acids using a chiral Cu-salen complex as a phase transfer catalyst
Belokon', YN
Davies, RG
North, M
[J]. TETRAHEDRON LETTERS, 2000, 41 (37) : 7245 - 7248
[9] SCOPE AND LIMITATIONS OF THE REDUCTIVE COUPLING OF AROMATIC ALDIMINE DERIVATIVES WITH FORMATION OF 1,2-DIARYLETHYLENEDIAMINE UNITS, USING LOW-VALENT TITANIUM REAGENTS
BETSCHART, C
SCHMIDT, B
SEEBACH, D
[J]. HELVETICA CHIMICA ACTA, 1988, 71 (08) : 1999 - 2021
[10] Brown RCD, 2001, ANGEW CHEM INT EDIT, V40, P4496, DOI 10.1002/1521-3773(20011203)40:23<4496::AID-ANIE4496>3.0.CO

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