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
[1]  
Abell A.D., 2004, Organophosphorus Reagents, P99
[2]   Sustainable Synthetic Methods: Domino Construction of Dihydropyridin-4-ones and β-Amino Esters in Aqueous Ethanol [J].
Alaimo, Peter J. ;
O'Brien, Robert ;
Johnson, Adam W. ;
Slauson, Sarah R. ;
O'Brien, Jeannette M. ;
Tyson, Elizabeth L. ;
Marshall, Amanda-Lynn ;
Ottinger, Colleen E. ;
Chacon, Jon G. ;
Wallace, Lorien ;
Paulino, Corey Y. ;
Connell, Sarah .
ORGANIC LETTERS, 2008, 10 (22) :5111-5114
[3]   Green Chemistry: Principles and Practice [J].
Anastas, Paul ;
Eghbali, Nicolas .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) :301-312
[4]  
[Anonymous], 2006, ANGEW CHEM-GER EDIT
[5]  
[Anonymous], 2003, ANGEW CHEM
[6]   Group 13 compounds incorporating salen ligands [J].
Atwood, DA ;
Harvey, MJ .
CHEMICAL REVIEWS, 2001, 101 (01) :37-52
[7]   One-pot multi-step synthesis: a challenge spawning innovation [J].
Broadwater, SJ ;
Roth, SL ;
Price, KE ;
Kobaslija, M ;
McQuade, DT .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (16) :2899-2906
[8]   The mitsunobu reaction: Origin, mechanism, improvements, and applications [J].
But, Tracy Yuen Sze ;
Toy, Patrick H. .
CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (11) :1340-1355
[9]   Utilisation of homogeneous and supported chiral metal(salen) complexes in asymmetric catalysis [J].
Canali, L ;
Sherrington, DC .
CHEMICAL SOCIETY REVIEWS, 1999, 28 (02) :85-93
[10]   Ph3As-catalyzed Wittig-type olefination of aldehydes with diazoacetate in the presence of Na2S2O4 [J].
Cao, Peng ;
Li, Chuan-Ying ;
Kang, Yan-Biao ;
Xie, Zuowei ;
Sun, Xiu-Li ;
Tang, Yong .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (17) :6628-6630