Synthesis of aryl α-keto esters via the rearrangement of aryl cyanohydrin carbonate esters

被引：41
作者：
Thasana, N
Prachyawarakorn, V
Tontoolarug, S
Ruchirawat, S
机构：
[1] Chulabhorn Res Inst, Bangkok 10210, Thailand
[2] Mahidol Univ, Dept Chem, Bangkok 10400, Thailand
[3] Mahidol Univ, Programme Res & Dev Synthet Drugs, Inst Sci & Technol Res & Dev, Bangkok 10400, Thailand
来源：
TETRAHEDRON LETTERS | 2003年 / 44卷 / 05期
关键词：
D O I：
10.1016/S0040-4039(02)02725-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A facile synthesis of aryl alpha-keto esters is reported involving the rearrangement of aryl cyanohydrin carbonate esters induced by the alpha-carbanion to the nitrile group generated by LDA. However, under similar conditions, an o-benzyloxycyanohydrin carbonate ester rearranged via a domino reaction leading to 2-phenylbenzofuran-3-carboxylic acid. (C) 2003 Elsevier Science Ltd. All rights reserved.
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页码：1019 / 1021
页数：3
相关论文
共 26 条
[1]   Lewis acid mediated [3+2] cycloaddition of allylgermane: stereoselective synthesis of germyl substituted tetrahydrofurans [J].
Akiyama, T ;
Suzuki, M .
CHEMICAL COMMUNICATIONS, 1997, (24) :2357-2358
[2]   CYANO-CARBONATES .2. EFFICIENT LATENT ACYL CARBANIONS IN 1,4-ADDITIONS [J].
AU, AT .
SYNTHETIC COMMUNICATIONS, 1984, 14 (08) :749-753
[3]   A stereoselective synthesis of dl-threo-methylphenidate:: Preparation and biological evaluation of novel analogues [J].
Axten, JM ;
Krim, L ;
Kung, HF ;
Winkler, JD .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9628-9629
[4]   Highly diastereoselective TiCl4 mediated addition of (E)-cinnamyl(tributyl)tin to α-keto esters [J].
Basavaiah, D ;
Sreenivasulu, B .
TETRAHEDRON LETTERS, 2002, 43 (16) :2987-2990
[5]  
Basavaiah D, 1999, SYNLETT, P1249
[6]   CAPTODATIVE RATE ENHANCEMENTS IN THE METHYLENECYCLOPROPANE REARRANGEMENT [J].
CREARY, X ;
MEHRSHEIKHMOHAMMADI, ME .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (14) :2664-2668
[7]  
DUGAS H, 1999, BIOORGANIC CHEM CHEM
[8]  
Hollwedel F, 1998, SYNTHESIS-STUTTGART, P1241
[9]   ELIMINATIVE RING FISSION OF 1,2,4-TRIOXAN-5-ONES - A NEW APPROACH TO ALPHA-KETO ACIDS [J].
JEFFORD, CW ;
ROSSIER, JC ;
BOUKOUVALAS, J .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (23) :1701-1702
[10]   A convenient preparation of α-keto esters by the Grignard reaction on N-acylpyrazoles [J].
Kashima, C ;
Shirahata, Y ;
Tsukamoto, Y .
HETEROCYCLES, 1998, 49 :459-464
123