A novel chiral pentamine ligand for enantioselective α-alkylation of acyclic lithium amide enolates.: Optimization of chiral ligands for asymmetric reactions using solid-phase organic synthesis

被引：17

作者：

Matsuo, J ^{[1
]}

Odashima, K ^{[1
]}

Kobayashi, S ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 02期

关键词：

D O I：

10.1021/ol990624d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A novel pentamine ligand has been developed for enantioselective alpha-alkylation of simple acyclic lithium amide enolates. It has been demonstrated that solid phase organic synthesis provides a powerful and rapid method for finding efficient chiral ligands.

引用

页码：345 / 347

页数：3

共 22 条

[1] Design and solid-phase synthesis of chiral acyclic and cyclic diamine ligands
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[2] Solid-phase development of chiral phosphoramidite ligands for enantioselective conjugate addition reactions
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CHEMISTRY-A EUROPEAN JOURNAL, 2002, 8 (20) : 4767 - 4780
[3] Solid phase asymmetric alkylation reactions using 2-imidazolidinone chiral auxiliary
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TETRAHEDRON LETTERS, 2009, 50 (28) : 4015 - 4018
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Ma, L
Williard, PG
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U356 - U356
[5] ASYMMETRIC ALKYLATION REACTIONS OF CHIRAL IMIDE ENOLATES - A PRACTICAL APPROACH TO THE ENANTIOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED CARBOXYLIC-ACID DERIVATIVES
EVANS, DA
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[6] Asymmetric Glycolate Alkylation Reactions in the Solid Phase Using 2-Imidazolidinone Chiral Auxiliary
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[7] Solid-phase synthesis of chiral 3,4-diazaphospholanes and their application to catalytic asymmetric allylic alkylation
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Clark, TP
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) : 5428 - 5432
[8] Design and synthesis of a new polymer-supported Evans-type oxazolidinone: an efficient chiral auxiliary in the solid-phase asymmetric alkylation reactions
Kotake, T
Hayashi, Y
Rajesh, S
Mukai, Y
Takiguchi, Y
Kimura, T
Kiso, Y
TETRAHEDRON, 2005, 61 (15) : 3819 - 3833
[9] Chiral catalyst optimization using both solid-phase and liquid-phase methods in asymmetric aza Diels-Alder reactions
Kobayashi, S
Kusakabe, K
Ishitani, H
ORGANIC LETTERS, 2000, 2 (09) : 1225 - 1227
[10] Stereoselective reactions. Part 30: Enantioselective alkylation of the lithium enolates of six-membered cyclic ketones using tetradentate chiral amines in the presence of lithium bromide
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Yasukata, T.
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