Iron(II)-Derived Lewis Acid/Surfactant Combined Catalysis for the Enantioselective Mukaiyama Aldol Reaction in Pure Water

被引：21

作者：

Lafantaisie, Mathieu ^{[1
]}

Mirabaud, Anais ^{[1
]}

Plancq, Baptiste ^{[1
]}

Ollevier, Thierry ^{[1
]}

机构：

[1] Univ Laval, Dept Chim, Quebec City, PQ G1V 0A6, Canada

来源：

CHEMCATCHEM | 2014年 / 6卷 / 08期

基金：

加拿大自然科学与工程研究理事会; 加拿大创新基金会;

关键词：

aldol reaction; enantioselectivity; iron; Lewis acids; surfactants; SURFACTANT-COMBINED CATALYST; SILYL ENOL ETHERS; AQUEOUS-MEDIA; ORGANIC-REACTIONS; ACID CATALYSTS; ASYMMETRIC CATALYSIS; LIGANDS; IRON; HYDROXYMETHYLATION; TRIFLATE;

D O I：

10.1002/cctc.201402029

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The catalytic asymmetric Mukaiyama aldol reaction in pure water was performed by using a combination of iron(II) dodecyl sulfate, a chiral bipyridine ligand, and benzoic acid. By using the obtained iron(II)-derived Lewis acid/surfactant combined catalyst, the desired products were afforded in good yields with high diastereo- and enantioselectivities.

引用

页码：2244 / 2247

页数：4

共 50 条

[1] Acid/base catalysis by pure water: The aldol reaction
Zhang, XY
Houk, KN
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (24): : 9712 - 9716
[2] Catalysis of Mukaiyama Aldol Reactions by a Tricyclic Aluminum Alkoxide Lewis Acid
Raders, Steven M.
Verkade, John G.
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15): : 5417 - 5428
[3] Highly enantioselective Mukaiyama aldol reaction in aqueous conditions using a chiral iron(II) bipyridine catalyst
Ollevier, Thierry
Plancq, Baptiste
CHEMICAL COMMUNICATIONS, 2012, 48 (17) : 2289 - 2291
[4] Highly enantioselective vinylogous aldol reaction of dioxinone-derived silyl diene by combined Lewis acid catalyst
Qi, Shuai
Ran, Qianping
Liu, Chang
Li, Bo
Zhang, Xiao
ARKIVOC, 2022, : 282 - 295
[5] Role of Water in Mukaiyama-Aldol Reaction Catalyzed by Lanthanide Lewis Acid: A Computational Study
Hatanaka, Miho
Morokuma, Keiji
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (37) : 13972 - 13979
[6] Crucial role of the ligand of silyl Lewis acid in the Mukaiyama aldol reaction
Ishihara, K
Hiraiwa, Y
Yamamoto, H
CHEMICAL COMMUNICATIONS, 2002, (15) : 1564 - 1565
[7] HIGHLY ENANTIOSELECTIVE CATALYSIS OF THE MUKAIYAMA ALDOL REACTION BY BINOL-TI PERFLUOROPHENOXIDE AND ENOXYSILACYCLOBUTANE
MATSUKAWA, S
MIKAMI, K
TETRAHEDRON-ASYMMETRY, 1995, 6 (10) : 2571 - 2574
[8] Iron-Modified Mesoporous Silica as an Efficient Solid Lewis Acid Catalyst for the Mukaiyama Aldol Reaction
Xu, Wan
Ollevier, Thierry
Kleitz, Freddy
ACS CATALYSIS, 2018, 8 (03): : 1932 - 1944
[9] Dicationic phosphonium salts: Lewis acid initiators for the Mukaiyama-aldol reaction
Barrado, Alejandro G.
Bayne, Julia M.
Johnstone, Timothy C.
Lehmann, Christian W.
Stephan, Douglas W.
Alcarazo, Manuel
DALTON TRANSACTIONS, 2017, 46 (46) : 16216 - 16227
[10] Lewis Base Catalysis of the Mukaiyama Directed Aldol Reaction: 40Years of Inspiration and Advances
Beutner, Gregory L.
Denmark, Scott E.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) : 9086 - 9096

← 1 2 3 4 5 →