Facile synthesis of L-Dopa tert-butyl cater by catalytic enantioselective phase-transfer alkylation

被引：77

作者：

Ooi, T

Kameda, M

Tannai, H

Maruoka, K ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan

[2] Hokkaido Univ, Grad Sch Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 43期

关键词：

alkylation; chiral phase-transfer catalysis; L-Dopa esters; glycine derivatives;

D O I：

10.1016/S0040-4039(00)01443-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Facile asymmetric synthesis of L-Dopa and related amino acid esters has been achieved by phase-transfer catalysis of the rationally designed C-2-symmetric chiral quaternary ammonium salts 1. The 'scale-up' experiment performed with 5.00 g of tert-butyl glycinate-benzophenone Schiff base (2) represents the practical aspect of our approach. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：8339 / 8342

页数：4

共 9 条

[1] AHMED G, 1994, BIOTECHNOL LETT, V16, P367
[2] ESTERS OF L-DOPA - STRUCTURE-HYDROLYSIS RELATIONSHIPS AND ABILITY TO INDUCE CIRCLING BEHAVIOR IN AN EXPERIMENTAL-MODEL OF HEMIPARKINSONISM
BRUNNERGUENAT, M
CARRUPT, PA
LISA, G
TESTA, B
ROSE, S
THOMAS, K
JENNER, P
VENTURA, P
[J]. JOURNAL OF PHARMACY AND PHARMACOLOGY, 1995, 47 (10) : 861 - 869
[3] COOPER DR, 1987, J PHARM PHARMACOL, V39, P635
[4] MARREL C, 1985, EUR J MED CHEM, V20, P459
[5] SYNTHESIS OF SYMMETRICAL AND ASYMMETRIC DIAMIDES OF CITRIC-ACID AND AMINO-ACIDS
MILEWSKA, MJ
CHIMIAK, A
[J]. AMINO ACIDS, 1994, 7 (01) : 89 - 96
[6] Practical catalytic enantioselective synthesis of α,α-dialkyl-α-amino acids by chiral phase-transfer catalysis
Ooi, T
Takeuchi, M
Kameda, M
Maruoka, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (21) : 5228 - 5229
[7] Molecular design of a C2-symmetric chiral phase-transfer catalyst for practical asymmetric synthesis of α-amino acids
Ooi, T
Kameda, M
Maruoka, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (27) : 6519 - 6520
[8] SYNTHESIS AND PROTEIN-TYROSINE KINASE INHIBITORY ACTIVITY OF POLYHYDROXYLATED STILBENE ANALOGS OF PICEATANNOL
THAKKAR, K
GEAHLEN, RL
CUSHMAN, M
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (20) : 2950 - 2955
[9] ALTERATIONS TO THE CATALYTIC PROPERTIES OF POLYPHENOLOXIDASE IN DETERGENTLESS MICROEMULSIONS AND TERNARY WATER ORGANIC-SOLVENT MIXTURES
VULFSON, EN
AHMED, G
GILL, I
KOZLOV, IA
GOODENOUGH, PW
LAW, BA
[J]. BIOTECHNOLOGY LETTERS, 1991, 13 (02) : 91 - 96

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