An efficient synthesis of 2,3,5-trisubstituted furans from α,β-unsaturated ketones

被引:43
作者
Brown, CD [1 ]
Chong, JM [1 ]
Shen, LX [1 ]
机构
[1] Univ Waterloo, Guelph Waterloo Ctr Grad Work Chem, Dept Chem, Waterloo, ON N2L 3G1, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
furans; alkynes; cyclization; regioselective;
D O I
10.1016/S0040-4020(99)00898-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple, regioselective synthesis of 2,3,5-trisubstituted furans is described. Conjugate addition of alkynylboronates to alpha,beta-unsaturated ketones, followed by acid-catalyzed cyclization of the resulting gamma-alkynyl ketones affords trisubstituted furans in 31-97% overall yields. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:14233 / 14242
页数:10
相关论文
共 25 条
[1]   THE PALLADIUM-CATALYZED SYNTHESIS OF 2,3,5-TRISUBSTITUTED FURANS FROM 2-PROPARGYL-1,3-DICARBONYL COMPOUNDS AND VINYLIC OR ARYL TRIFLATES OR HALIDES [J].
ARCADI, A ;
CACCHI, S ;
LAROCK, RC ;
MARINELLI, F .
TETRAHEDRON LETTERS, 1993, 34 (17) :2813-2816
[2]   Synthesis of functionalised furans and pyrroles through annulation reactions of 4-pentynones. [J].
Arcadi, A ;
Rossi, E .
TETRAHEDRON, 1998, 54 (50) :15253-15272
[3]  
BICKING KJ, 1978, J MED CHEM, V21, P1011
[4]   HETEROGENEOUS CATALYSIS BY SALTS AND SOLVENTS .3. SYNTHESIS OF ALPHA, BETA-UNSATURATED CARBONYL-COMPOUNDS FROM SILYL ENOL ETHERS [J].
BOYER, J ;
CORRIU, RJP ;
PERZ, R ;
REYE, C .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 184 (02) :157-166
[5]   ORGANOBORANES .31. A SIMPLE PREPARATION OF BORONIC ESTERS FROM ORGANO-LITHIUM REAGENTS AND SELECTED TRIALKOXYBORANES [J].
BROWN, HC ;
COLE, TE .
ORGANOMETALLICS, 1983, 2 (10) :1316-1319
[6]   A convenient preparation of (E)-3-penten-2-one [J].
Chiu, P ;
Wong, ST .
SYNTHETIC COMMUNICATIONS, 1998, 28 (24) :4513-4516
[7]  
CHONG JM, 1998, 81 CAN SOC CHEM C EX
[8]  
CHONG JM, UNPUB J AM CHEM SOC
[9]   THE SYNTHESIS OF HETEROAROMATIC PROSTACYCLIN ANALOGS VIA KETO ALKYNE CYCLIZATION [J].
COOK, S ;
HENDERSON, D ;
RICHARDSON, KA ;
TAYLOR, RJK ;
SAUNDERS, J ;
STRANGE, PG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (08) :1825-1831
[10]   BORON-TRIFLUORIDE ETHERATE MEDIATED 1,4-ADDITION OF (1-ALKYNYL)DIISOPROPOXYBORANES TO ALPHA,BETA-UNSATURATED KETONES - A CONVENIENT NEW ROUTE TO 3-ALKYNYL KETONE SYNTHESIS [J].
FUJISHIMA, H ;
TAKADA, E ;
HARA, S ;
SUZUKI, A .
CHEMISTRY LETTERS, 1992, (04) :695-698