Electrosynthesis of α-arylated β-substituted cyclopropylphosphonates.: Synthesis of a phosphonic analogue of minalcipran

被引：26
作者：
Duquenne, C
Goumain, S
Jubault, P
Feasson, C
Quirion, JC
机构：
[1] INSA, IRCOF, CNRS, Lab Heterochim Organ, F-76130 Mt St Aignan, France
[2] Univ Rouen, F-76130 Mt St Aignan, France
来源：
ORGANIC LETTERS | 2000年 / 2卷 / 04期
关键词：
D O I：
10.1021/ol991301k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] The synthesis of alpha-arylated beta-substituted cyclopropylphosphonates was efficiently achieved by electroreduction of diethyl alpha,alpha-dichlorobenzylphosphonate in the presence of Michael accepters in a one compartment cell equipped with a magnesium sacrificial anode.
引用
收藏
页码：453 / 455
页数：3
相关论文
共 25 条
[1]   1-ARYL-2-(AMINOMETHYL)CYCLOPROPANECARBOXYLIC ACID-DERIVATIVES - A NEW SERIES OF POTENTIAL ANTIDEPRESSANTS [J].
BONNAUD, B ;
COUSSE, H ;
MOUZIN, G ;
BRILEY, M ;
STENGER, A ;
FAURAN, F ;
COUZINIER, JP .
JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (02) :318-325
[2]   CONFORMATIONAL EFFECTS OF SUBSTITUTING METHIONINE WITH (2S,3S)-2,3-METHANOMETHIONINE IN PHE-MET-ARG-PHE-NH2 [J].
BURGESS, K ;
HO, KK ;
PETTITT, BM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (01) :54-65
[3]   THE EFFECT OF THE DIETHYLPHOSPHONATE GROUP ON FREE-RADICAL STABILITIES [J].
CREARY, X ;
BENAGE, B ;
MEHRSHEIKHMOHAMMADI, ME ;
BAYS, JP .
TETRAHEDRON LETTERS, 1985, 26 (20) :2383-2386
[4]  
DEMEIJERE A, 1990, SYNLETT, P20
[5]   PHOSPHONATES AS ANALOGS OF NATURAL PHOSPHATES [J].
ENGEL, R .
CHEMICAL REVIEWS, 1977, 77 (03) :349-367
[6]   First synthesis of α-fluorinated cyclopropylphosphonates using magnesium electrochemical activation [J].
Goumain, S ;
Jubault, P ;
Feasson, C ;
Quirion, JC .
TETRAHEDRON LETTERS, 1999, 40 (46) :8099-8101
[7]   The stereoselective synthesis of cyclopropylphosphonate analogs of nucleotides [J].
Hah, JH ;
Gil, JM ;
Oh, DY .
TETRAHEDRON LETTERS, 1999, 40 (47) :8235-8238
[8]   Mechanism of action of vitamin B-12. A new test for free radical intermediates using a cyclopropane model for the methylmalonyl-CoA to succinyl-CoA carbon skeleton rearrangement [J].
He, M ;
Dowd, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (03) :711-711
[9]   SOLVENT EFFECT IN A PARTIAL ASYMMETRIC SYNTHESIS .I. [J].
INOUYE, Y ;
INAMASU, S ;
HORIIKE, M ;
OHNO, M .
TETRAHEDRON, 1968, 24 (07) :2907-&
[10]   A new and efficient electrosynthesis of polysubstituted cyclopropylphosphonates, using electrochemically activated magnesium [J].
Jubault, P ;
Goumain, S ;
Feasson, C ;
Collignon, N .
TETRAHEDRON, 1998, 54 (49) :14767-14778
123