Enantioselective catalytic synthesis of ethyl mandelate derivatives using Rh(I)-NHC catalysts and organoboron reagents

被引：15

作者：

Marques, Carolina S.

Burke, Anthony J. ^{[1
]}

机构：

[1] Univ Evora, Dept Chem, P-7000 Evora, Portugal

来源：

TETRAHEDRON-ASYMMETRY | 2013年 / 24卷 / 11期

关键词：

GLYOXYLATE-ENE REACTION; OXIDATION/BENZILIC ESTER REARRANGEMENT; ALPHA-HYDROXYCARBOXYLIC ACIDS; ARYLBORONIC ACIDS; ALPHA; BETA-UNSATURATED KETONES; ADDITION-REACTIONS; RHODIUM COMPLEXES; HYDROXY ESTERS; BORONIC ACIDS; BORIC-ACID;

D O I：

10.1016/j.tetasy.2013.04.011

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Herein we describe for the first time the enantioselective catalytic arylation of ethyl glyoxalate using phenylboron reagents and chiral rhodium(I)-NHC catalysts. (KOBu)-Bu-t was the base of choice, along with tert-amyl alcohol as the solvent. A novel chiral bis-imidazolium salt was synthesized and evaluated for the first time in this catalytic transformation. Although moderate enantioselectivities (up to 34% ee) were obtained for the phenylation reaction, despite the excellent yields, very low enantioselectivities were obtained using other arylboronic acids with a variety of chiral rhodium(I)-NHC catalysts. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：628 / 632

页数：5

共 48 条

[11] Synthesis of optically active amino sugar derivatives using catalytic enantioselective hetero-Diels-Alder reactions
Zhuang, W
Thorhauge, J
Jorgensen, KA
CHEMICAL COMMUNICATIONS, 2000, (06) : 459 - 460
[12] CATALYTIC ENANTIOSELECTIVE CONJUGATE ADDITION OF GRIGNARD-REAGENTS TO 2-CYCLOHEXEN-1-ONE USING CHIRAL AMINOTROPONEIMINATOCOPPER(I) COMPLEXES
VILLACORTA, GM
AHN, KH
LIPPARD, SJ
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 196 : 336 - INOR
[13] Catalytic asymmetric synthesis of α-amino acid derivatives and peptides using chiral phase-transfer catalysts
Maruoka, K
PROCEEDINGS OF THE JAPAN ACADEMY SERIES B-PHYSICAL AND BIOLOGICAL SCIENCES, 2003, 79 (07): : 181 - 189
[14] Asymmetric synthesis of homoproline derivatives via Rh(I)catalyzed hydrogenation using chiral bisphosphines as ligands
Zhang, YH
Park, JH
Lee, SG
TETRAHEDRON-ASYMMETRY, 2004, 15 (14) : 2209 - 2212
[15] Enantioselective synthesis of multifunctionalized 4H-pyran derivatives using bifunctional thiourea-tertiary amine catalysts
Zhao, Sheng-Li
Zheng, Chang-Wu
Zhao, Gang
TETRAHEDRON-ASYMMETRY, 2009, 20 (09) : 1046 - 1051
[16] HOMOGENEOUS CATALYTIC-HYDROGENATION OF OLEFINS USING RHODIUM(I) COMPOUNDS WITH 2-AMINOPYRIDINE DERIVATIVES AS CATALYSTS
ZUBER, M
SZUBERLA, WA
PRUCHNIK, FP
JOURNAL OF MOLECULAR CATALYSIS, 1986, 38 (03): : 309 - 314
[17] Catalytic enantioselective reactions .8. Catalytic enantioselective addition of diethylzinc to aldehydes using (2S,3S)-(-)-1,4-diamino-2,3-butanediol derivatives as chiral catalysts
Cho, BT
Kim, N
SYNTHETIC COMMUNICATIONS, 1996, 26 (12) : 2273 - 2280
[18] SYNTHESIS AND REACTIVITY OF BINUCLEAR TROPOCORONAND AND RELATED ORGANOCOPPER(I) COMPLEXES - CATALYTIC ENANTIOSELECTIVE CONJUGATE ADDITION OF GRIGNARD-REAGENTS TO 2-CYCLOHEXEN-1-ONE
VILLACORTA, GM
RAO, CP
LIPPARD, SJ
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (10) : 3175 - 3182
[19] Enantioselective Synthesis of Alkyne-Substituted Quaternary Carbon Stereogenic Centers through NHC-Cu-Catalyzed Allylic Substitution Reactions with (i-Bu)2(Alkynyl)aluminum Reagents
Dabrowski, Jennifer A.
Gao, Fang
Hoveyda, Amir H.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (13) : 4778 - 4781
[20] Enantioselective Total Synthesis of Chondrosterins I and J by Catalytic Asymmetric Intramolecular Aldol Reaction Using Chiral Diamine Catalyst
Kawamoto, Yuichiro
Ozone, Daiki
Kobayashi, Toyoharu
Ito, Hisanaka
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (26) : 4050 - 4058

← 1 2 3 4 5 →