Facile synthesis of α-substituted acrylate esters

被引:47
作者
Hin, B [1 ]
Majer, P [1 ]
Tsukamoto, T [1 ]
机构
[1] Guilford Pharmaceut Inc, Baltimore, MD 21224 USA
关键词
D O I
10.1021/jo026101s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of 5-monosubstituted Meldrum's acids with dimethylmethyleneimmonium iodide (Eschenmoser's iodide salt) in methanol gives a-substituted acrylate methyl esters in good yields. Easy access to 5-monosubstituted Meldrum's acids allowed us to synthesize a wide variety of a-substituted acrylate methyl esters. The reaction conditions are mild and tolerate many functional groups commonly used in organic synthesis; thus, this new method has potential as an alternative to conventional preparative methods for a-substituted acrylate esters.
引用
收藏
页码:7365 / 7368
页数:4
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共 27 条
[1]  
Boisbrun M, 2000, EUR J ORG CHEM, V2000, P3051, DOI 10.1002/1099-0690(200009)2000:17<3051::AID-EJOC3051>3.0.CO
[2]  
2-3
[3]   Stereochemically controlled syntheses of indole-substituted dihydrofuran-2-ones and a pyrrolidin-2-one [J].
Boisbrun, M ;
Kovács-Kulyassa, A ;
Jeannin, L ;
Sapi, J ;
Toupet, L ;
Laronze, JY .
TETRAHEDRON LETTERS, 2000, 41 (50) :9771-9775
[4]   Phosphinic acid inhibitors of matrix metalloproteinases [J].
Caldwell, CG ;
Sahoo, SP ;
Polo, SA ;
Eversole, RR ;
Lanza, TJ ;
Mills, SG ;
Niedzwiecki, LM ;
IzquierdoMartin, M ;
Chang, BC ;
Harrison, RK ;
Kuo, DW ;
Lin, TY ;
Stein, RL ;
Durette, PL ;
Hagmann, WK .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (03) :323-328
[5]  
CHAN CC, 1984, SYNTHESIS-STUTTGART, P224
[6]   An efficient synthetic route to 2-(1,2-dithiolan-3-yl)acetic acid. Trisnorlipoic acid and amide derivatives. [J].
Chen, YS ;
Lawton, RG .
TETRAHEDRON LETTERS, 1997, 38 (33) :5785-5788
[7]   SYNTHESIS OF PARTIALLY MODIFIED RETRO-INVERSO SUBSTANCE-P ANALOGS AND THEIR BIOLOGICAL-ACTIVITY [J].
CHOREV, M ;
RUBINI, E ;
GILON, C ;
WORMSER, U ;
SELINGER, Z .
JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (02) :129-135
[8]   Partially modified retro-inverso pseudopeptides as non-natural ligands for the human class I histocompatibility molecule HLA-A2 [J].
Guichard, G ;
Connan, F ;
Graff, R ;
Ostankovitch, M ;
Muller, S ;
Guillet, JG ;
Choppin, J ;
Briand, JP .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (10) :2030-2039
[9]   THE REDUCTIVE ALKYLATION OF MELDRUM ACID [J].
HRUBOWCHAK, DM ;
SMITH, FX .
TETRAHEDRON LETTERS, 1983, 24 (45) :4951-4954
[10]   ONE POT SYNTHESIS OF MONOSUBSTITUTED ISOPROPYLIDENE MALONATES [J].
HUANG, X ;
XIE, LH .
SYNTHETIC COMMUNICATIONS, 1986, 16 (13) :1701-1707