Mukaiyama Aldol Reactions in Aqueous Media

被引:80
作者
Kitanosono, Taku [1 ]
Kobayashi, Shu [1 ]
机构
[1] Univ Tokyo, Dept Chem, Sch Sci, Bunkyo Ku, Hongo, Tokyo, Japan
基金
日本学术振兴会;
关键词
aldol reaction; asymmetric catalysis; green chemistry; Lewis acids; water; SILYL ENOL ETHERS; LEWIS-ACID CATALYSTS; DIELS-ALDER REACTIONS; SURFACTANT-COMBINED CATALYSTS; SUPPORTED SCANDIUM CATALYST; HOST-GUEST COMPLEXATION; CARBON BOND FORMATION; EFFECTIVE IONIC-RADII; ORGANIC-REACTIONS; COPPER(II) COMPLEXES;
D O I
10.1002/adsc.201300798
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Mukaiyama aldol reactions in aqueous media have been surveyed. While the original Mukaiyama aldol reactions entailed stoichiometric use of Lewis acids in organic solvents under strictly anhydrous conditions, Mukaiyama aldol reactions in aqueous media are not only suitable for green sustainable chemistry but are found to produce singular phenomena. These findings led to the discovery of a series of water-compatible Lewis acids such as lanthanide triflates in 1991. Our understanding on these beneficial effects in the presence of water will be deepened through the brilliant examples collected in this review.
引用
收藏
页码:3095 / 3118
页数:24
相关论文
共 203 条
[1]   Functionalization of Peptides and Proteins by Mukaiyama Aldol Reaction [J].
Alam, Jenefer ;
Keller, Thomas H. ;
Loh, Teck-Peng .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (28) :9546-9548
[2]   DESIGN AND SYNTHESIS OF MACROCYCLIC LIGANDS AND THEIR COMPLEXES OF LANTHANIDES AND ACTINIDES [J].
ALEXANDER, V .
CHEMICAL REVIEWS, 1995, 95 (02) :273-342
[3]  
[Anonymous], 2013, MARCHS ADV ORGANIC C
[4]   Iron(III) chloride as a water-compatible Lewis acid for diastereoselective aldol reactions in water in the presence of a surfactant [J].
Aoyama, N ;
Manabe, K ;
Kobayashi, S .
CHEMISTRY LETTERS, 2004, 33 (03) :312-313
[5]   STUDIES TOWARDS THE TOTAL SYNTHESIS OF TAXOIDS - AN EFFICIENT FORMAL TOTAL SYNTHESIS OF AN A-SECO TAXANE FRAMEWORK [J].
ARSENIYADIS, S ;
WANG, Q ;
YASHUNSKY, DV ;
KAOUDI, T ;
ALVES, RB ;
POTIER, P .
TETRAHEDRON LETTERS, 1995, 36 (10) :1633-1636
[6]   Ytterbium triflate catalysed allylation of aldehydes: An unusual benzoic acid induced acceleration [J].
Aspinall, HC ;
Greeves, N ;
McIver, EG .
TETRAHEDRON LETTERS, 1998, 39 (50) :9283-9286
[7]   The Role of Water in Lanthanide-Catalyzed Carbon-Carbon Bond Formation [J].
Averill, Derek J. ;
Dissanayake, Prabani ;
Allen, Matthew J. .
MOLECULES, 2012, 17 (02) :2073-2081
[8]  
Base C.F., 1976, The hydrolysis of cations
[9]   Enantioselective catalysis in water: Mukaiyama-aldol condensation promoted by copper complexes of bisoxazolines supported on poly(ethylene glycol) [J].
Benaglia, M ;
Cinquini, M ;
Cozzi, F ;
Celentano, G .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (22) :3401-3407
[10]   Total asymmetric synthesis of the putative structure of the cytotoxic diterpenoid (-)-sclerophytin A and of the authentic natural sclerophytins A and B [J].
Bernardelli, P ;
Moradei, OA ;
Friedrich, D ;
Yang, J ;
Gallou, F ;
Dyck, BP ;
Doskotch, RW ;
Lange, T ;
Paquette, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (37) :9021-9032