New transformations of 2-nitro-2,3-dihydrofurans to multi-functionalized dihydrofurans

被引:4
作者
Hwu, JR [1 ]
Sambaiah, T [1 ]
Chakraborty, SK [1 ]
机构
[1] Natl Tsing Hua Univ, Dept Chem, Synth Organ Lab, Hsinchu 30013, Taiwan
关键词
D O I
10.1016/S0040-4039(03)00463-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new type of transformation of 2-nitro-3-substituted-dihydrofurans to 4-formyl-2-hydroxy-3-substituted-2,3-dihydrofurans was accomplished in 63-84% yields by use of BF3.OEt2 in CH2Cl2 at -78 to 0degreesC. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3167 / 3169
页数:3
相关论文
共 30 条
[1]   OXIDATION AND ELIMINATION-REACTIONS STUDY IN A FORMAL SYNTHESIS OF (+/-)-FORSKOLIN [J].
ANIES, C ;
PANCRAZI, A ;
LALLEMAND, JY .
TETRAHEDRON LETTERS, 1995, 36 (12) :2075-2078
[2]  
ANIES C, 1994, TETRAHEDRON LETT, V35, P7771
[3]   Stereoselective synthesis of dihydrofurans under phase-transfer catalyzed conditions [J].
Arai, S ;
Nakayama, K ;
Suzuki, Y ;
Hatano, K ;
Shioiri, T .
TETRAHEDRON LETTERS, 1998, 39 (52) :9739-9742
[4]   GENERATION AND CYCLOADDITION REACTIONS OF 3-SUBSTITUTED-2-NITRO-1,3-DIENES [J].
BARCO, A ;
BENETTI, S ;
POLLINI, GP ;
SPALLUTO, G ;
ZANIRATO, V .
TETRAHEDRON LETTERS, 1991, 32 (22) :2517-2520
[5]   HETEROSUBSTITUTED NITROALKENES IN SYNTHESIS [J].
BARRETT, AGM .
CHEMICAL SOCIETY REVIEWS, 1991, 20 (01) :95-127
[6]   ALDOL AND MICHAEL ADDITIONS OF FLUORINATED NITROALKANES TO ALDEHYDES, KETONES, AND ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS [J].
BECK, AK ;
SEEBACH, D .
CHEMISCHE BERICHTE-RECUEIL, 1991, 124 (12) :2897-2911
[7]   SYNTHETIC STUDIES ON THE GINKGOLIDES - TOTAL SYNTHESIS OF (+/-)-BILOBALIDE [J].
CRIMMINS, MT ;
JUNG, DK ;
GRAY, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (08) :3146-3155
[8]   Asymmetric synthesis of 2,3-dihydrofurans by reaction of rhodium-stabilized vinylcarbenoids with vinyl ethers [J].
Davies, HML ;
Ahmed, G ;
Calvo, RL ;
Churchill, MR ;
Churchill, DG .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2641-2645
[9]   ABSOLUTE-CONFIGURATION OF NOVEL MARINE DITERPENOID UDOTEATRIAL HYDRATE SYNTHESIS AND CYTOTOXICITIES OF ENT-UDOTEATRIAL HYDRATE AND ITS ANALOGS [J].
GE, YT ;
KONDO, S ;
KATSUMURA, S ;
NAKATANI, K ;
ISOE, S .
TETRAHEDRON, 1993, 49 (46) :10555-10576
[10]   STUDIES ON ORGANOSILICON CHEMISTRY .119. NEW ACCESS TO CARBONYL YLIDES BY THE SILICON-BASED 1,3-ELIMINATION AND THEIR [3+2] CYCLOADDITIONS TO ACTIVATED ALKENES AND ALKYNES - ONE-STEP SYNTHESIS OF DIHYDROFURANS AND TETRAHYDROFURANS [J].
HOJO, M ;
OHKUMA, M ;
ISHIBASHI, N ;
HOSOMI, A .
TETRAHEDRON LETTERS, 1993, 34 (37) :5943-5946