Improving the Atom Efficiency of the Wittig Reaction by a "Waste as Catalyst/Co-catalyst" Strategy

被引:127
作者
Cao, Jun-Jie [1 ,2 ]
Zhou, Feng [1 ,2 ]
Zhou, Jian [1 ,2 ]
机构
[1] E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China
[2] E China Normal Univ, Dept Chem, Shanghai 200062, Peoples R China
基金
中国国家自然科学基金;
关键词
atom economy; Lewis bases; sustainable chemistry; tandem reactions; Wittig reaction; ASYMMETRIC TRANSFER HYDROGENATION; REDUCTIVE ALDOL REACTION; BETA-AMINO ESTERS; ENANTIOSELECTIVE CYANOSILYLATION; ORGANIC-SYNTHESIS; CONJUGATE REDUCTION; METAL-FREE; OLEFINATION; KETONES; EPOXIDATION;
D O I
10.1002/anie.201000896
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) Waste not want not: Reported is a strategy to improve the atom economy of the Wittig reaction by using it in tandem reactions that directly employ the wastePh3PO as an in-situ-generated Lewis base catalyst/co-catalyst in the next step (see scheme). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:4976 / 4980
页数:5
相关论文
共 111 条
[21]   Ionic liquid (molten salt) phase organometallic catalysis [J].
Dupont, J ;
de Souza, RF ;
Suarez, PAZ .
CHEMICAL REVIEWS, 2002, 102 (10) :3667-3691
[22]   INTRAMOLECULAR DIELS-ALDER REACTIONS OF 3H-PYRROLES RESULTING FROM THE THERMAL REARRANGEMENTS OF 2H-PYRROLES [J].
EDDAIF, A ;
LAURENT, A ;
MISON, P ;
PELLISSIER, N ;
CARRUPT, PA ;
VOGEL, P .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (25) :5548-5560
[23]  
Edmonds D., 2004, MODERN CARBONYL OLEF, P1
[24]  
Enders D., 2007, Angew. Chem, V119, P1590, DOI DOI 10.1002/ange.200603129
[25]   Asymmetric organocatalytic domino reactions [J].
Enders, Dieter ;
Grondal, Christoph ;
Huettl, Matthias R. M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1570-1581
[26]   Application of iminophosphorane-based methodologies for the synthesis of natural products [J].
Fresneda, PM ;
Molina, P .
SYNLETT, 2004, (01) :1-17
[27]   Thiourea-catalyzed enantioselective cyanosilylation of ketones [J].
Fuerst, DE ;
Jacobsen, EN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) :8964-8965
[28]   Recent Progress in Lewis Base Activation and Control of Stereoselectivity in the Additions of Trimethylsilyl Nucleophiles [J].
Gawronski, Jacek ;
Wascinska, Natalia ;
Gajewy, Jadwiga .
CHEMICAL REVIEWS, 2008, 108 (12) :5227-5252
[29]   RECENT ADVANCES IN THE STAUDINGER REACTION [J].
GOLOLOBOV, YG ;
KASUKHIN, LF .
TETRAHEDRON, 1992, 48 (08) :1353-1406
[30]   60 YEARS OF STAUDINGER REACTION [J].
GOLOLOBOV, YG ;
ZHMUROVA, IN ;
KASUKHIN, LF .
TETRAHEDRON, 1981, 37 (03) :437-472