A new strategy for the synthesis of optically active benzylic fluorides and corresponding five-membered heteroaromatic analogues

被引:25
作者
Gree, Danielle [1 ]
Gree, Rene [1 ]
机构
[1] Univ Rennes 1, CNRS, UMR 6510, Lab Synth & Electrosynth Organ, F-35042 Rennes, France
关键词
D O I
10.1016/j.tetlet.2007.06.007
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Benzylic fluorides, as well as five-membered heterocycles, have been obtained in high ee's through cycloaddition reactions starting from easily accessible optically active propargylic fluorides. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5435 / 5438
页数:4
相关论文
共 25 条
[1]  
[Anonymous], 1991, Fluorine in Bioorganic Chemistry
[2]  
BANKS RE, 1994, ORAGNOFLUORINE CHEM
[3]   Catalytic asymmetric fluorinations [J].
Bobbio, Carla ;
Gouverneur, Veronique .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (11) :2065-2075
[4]   Synthesis of propargylic fluorides from allenylsilanes [J].
Carroll, Laurence ;
Pacheco, Ma Carmen ;
Garcia, Ludivine ;
Gouverneur, Veronique .
CHEMICAL COMMUNICATIONS, 2006, (39) :4113-4115
[5]   Synthesis of the 9-fluoro analogues of disparlure [J].
Filmon, J ;
Grée, D ;
Grée, R .
JOURNAL OF FLUORINE CHEMISTRY, 2001, 107 (02) :271-273
[6]   ALKALI-METAL FLUORIDES AS EFFICIENT FLUORINATING AGENTS - ENANTIOCONTROLLED SYNTHESIS OF 2-FLUOROALKYL CARBOXYLATES AND 1-FLUOROALKYL BENZENES [J].
FRITZLANGHALS, E .
TETRAHEDRON-ASYMMETRY, 1994, 5 (06) :981-986
[7]   SYNTHESIS OF OPTICALLY-ACTIVE 1-FLUOROALKYL BENZENES [J].
FRITZLANGHALS, E .
TETRAHEDRON LETTERS, 1994, 35 (12) :1851-1854
[8]   High regio- and stereocontrol in the dehydroxy-fluorination of propargylic alcohols and the corresponding cobalt-carbonyl complexes [J].
Grée, D ;
Madiot, V ;
Grée, R .
TETRAHEDRON LETTERS, 1999, 40 (35) :6399-6402
[9]   Enantioselective fluorination reactions catalyzed by chiral palladium complexes [J].
Hamashima, Yoshitaka ;
Sodeoka, Mikiko .
SYNLETT, 2006, (10) :1467-1478
[10]  
HUDLICKY M, 1995, ACM MONOGRAPH, V187