Tandem bis-aldol reaction of ketones: A facile one-pot synthesis of 1,3-dioxanes in aqueous medium

被引:82
作者
Polshettiwar, Vivek [1 ]
Varma, Rajender S. [1 ]
机构
[1] US EPA, Natl Risk Management Res Lab, Sustainable Technol Div, Cincinnati, OH 45268 USA
关键词
D O I
10.1021/jo701337j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A novel tandem bis-aldol reaction of ketone with paraformaldehyde catalyzed by polystyrenesulfonic acid in aqueous medium delivers 1,3-dioxanes in high yield. This one-pot, operationally simple microwave-assisted synthetic protocol proceeds efficiently in water in the absence of organic solvent, with excellent yield.
引用
收藏
页码:7420 / 7422
页数:3
相关论文
共 25 条
[1]  
ADAMS DR, 1977, SYNTHESIS-STUTTGART, P661
[2]   Total synthesis of (+)-dactylolide through an efficient sequential peterson olefination and prins cyclization reaction [J].
Aubele, DL ;
Wan, SY ;
Floreancig, PE .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (22) :3485-3488
[3]   Gold- or platinum-catalyzed tandem cycloisomerization/Prins-type cyclization reactions [J].
Barluenga, J ;
Diéguez, A ;
Fernández, A ;
Rodríguez, F ;
Fañanás, FJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (13) :2091-2093
[4]   Formal synthesis of (+)-SCH 351448: the Prins cyclization approach [J].
Chan, Kok-Ping ;
Ling, Yvonne Hui ;
Loh, Teck-Peng .
CHEMICAL COMMUNICATIONS, 2007, (09) :939-941
[5]   Synthesis of novel 2,6-disubstituted-3,4-dimethylidene tetrahydropyrans via Prins-type cyclization [J].
Cho, YS ;
Karupaiyan, K ;
Kang, HJ ;
Pae, AN ;
Cha, JH ;
Koh, HY .
CHEMICAL COMMUNICATIONS, 2003, (18) :2346-2347
[6]   Microwave-assisted synthesis in water as solvent [J].
Dallinger, Doris ;
Kappe, C. Oliver .
CHEMICAL REVIEWS, 2007, 107 (06) :2563-2591
[7]   The condensation of paraformaldehyde with aromatic ketones [J].
Fuson, RC ;
Ross, WE ;
McKeever, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1938, 60 :2935-2936
[8]   Hydrophobic, low-loading and alkylated polystyrene-supported sulfonic acid for several organic reactions in water: remarkable effects of both the polymer structures and loading levels of sulfonic acids [J].
Iimura, S ;
Manabe, K ;
Kobayashi, S .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (14) :2416-2418
[9]   Racemization in prins cyclization reactions [J].
Jasti, Ramesh ;
Rychnovsky, Scott D. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (41) :13640-13648
[10]   Aqueous N-heterocyclization of primary amines and hydrazines with dihalides:: Microwave-assisted syntheses of N-azacycloalkanes, isoindole, pyrazole, pyrazolidine, and phthalazine derivatives [J].
Ju, YH ;
Varma, RS .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) :135-141