Unexpected formation of tetrasubstituted 2,3-dihydrofurans from the reactions of β-keto polyfluoroalkanesulfones with aldehydes

被引:69
作者
Xing, CH [1 ]
Zhu, SZ [1 ]
机构
[1] Chinese Acad Sci, Key Lab Organofluorine Chem, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
关键词
D O I
10.1021/jo049317y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Catalyzed by piperidine, the reactions of beta-keto polyfluoroalkanesulfones with aromatic aldehydes afforded the unexpected tetrasubstituted 2,3-dihydrofurans in good yields, probably proceeding through the normal Knoevenagel condensation products. This reaction provided an efficient and novel method for the stereoselective synthesis of fluorine-containing tetrasubstituted trans-2,3-dihydrofurans.
引用
收藏
页码:6486 / 6488
页数:3
相关论文
共 25 条
[1]   Diastereoselective synthesis of 4,5-dihydrofurans by iodoenolcyclisation of 2-allyl-1,3-dicarbonyl compounds [J].
Antonioletti, R ;
Malancona, S ;
Bovicelli, P .
TETRAHEDRON, 2002, 58 (43) :8825-8831
[2]   ACIDITIES OF CARBON ACIDS .7. CONJUGATION AND STRAIN IN SOME CYCLOPROPYL ANIONS [J].
BORDWELL, FG ;
VANIER, NR ;
MATTHEWS, WS ;
HENDRICKSON, JB ;
SKIPPER, PL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (24) :7160-7162
[3]   Green chemistry approaches to the synthesis of 5-alkoxycarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones by a three-component coupling of one-pot condensation reaction:: Comparison of ethanol, water, and solvent-free conditions [J].
Bose, DS ;
Fatima, L ;
Mereyala, HB .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) :587-590
[4]   Stereoselective synthesis of tetrasubstituted 2,3-dihydrofurans by one-step cyclization of β-ketosulfides of benzothiazole and aldehydes in ionic liquids [J].
Calò, V ;
Scordari, F ;
Nacci, A ;
Schingaro, E ;
D'Accolti, L ;
Monopoli, A .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4406-4409
[5]  
CARRIDO JL, 1998, J ORG CHEM, V63, P9406
[6]  
Goumont R, 1999, EUR J ORG CHEM, V1999, P2969
[7]   Domino Michael-O-alkylation reaction:: one-pot synthesis of 2,4-diacylhydrofuran derivatives and its application to antitumor naphthofuran synthesis [J].
Hagiwara, H ;
Sato, K ;
Nishino, D ;
Hoshi, T ;
Suzuki, T ;
Ando, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (22) :2946-2957
[8]  
HANACK M, 1991, SYNTHESIS-STUTTGART, P1205
[9]   TRIFLAMIDES (CF3SO2N LESS-THAN) - SURVEY [J].
HENDRICK.JB ;
BERGERON, R ;
GIGA, A ;
STERNBAC.D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (10) :3412-3413
[10]   TRIFLONES (CF3SO2C) - SURVEY OF REACTIVITY AND SYNTHETIC UTILITY [J].
HENDRICKSON, JB ;
GIGA, A ;
WAREING, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (07) :2275-2276