Mild, Rapid, and Inexpensive Microwave-Assisted Synthesis of Allylic and Propargylic Esters

被引:3
作者
Gill, Monica A. [1 ]
Manthorpe, Jeffrey M. [1 ]
机构
[1] Carleton Univ, Dept Chem, Ottawa, ON K1S 5B6, Canada
基金
加拿大创新基金会; 加拿大自然科学与工程研究理事会;
关键词
Allylic esters; esterification; microwave-assisted synthesis; mixed anhydride; propargylic esters; CLAISEN REARRANGEMENT; CARBOXYLIC ESTERS; DIHYDROXYLATION; REAGENTS;
D O I
10.1080/00397911.2011.640970
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A variety of allylic and propargylic esters were rapidly prepared via microwave heating of their corresponding mixed anhydride derived from pivaloyl chloride. The reaction conditions were modified to account for the sterics of the alcohol and the electronics of the carboxylic acid. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.
引用
收藏
页码:1460 / 1468
页数:9
相关论文
共 35 条
[1]   Synthesis and reactivity of π-electron-dericient (arylsulfonyl) acetates [J].
Alonso, DA ;
Nájera, C ;
Varea, M .
HELVETICA CHIMICA ACTA, 2002, 85 (12) :4287-4305
[2]   Synthesis of 2,6-dideoxysugars via ring-closing olefinic metathesis [J].
Andreana, PR ;
McLellan, JS ;
Chen, YC ;
Wang, PG .
ORGANIC LETTERS, 2002, 4 (22) :3875-3878
[3]  
Armstrong A., E EROS ENCY REAGENTS
[4]   FACILE SYNTHESIS OF CARBOXAMIDES BY USING 1-METHYL-2-HALOPYRIDINIUM IODIDES AS COUPLING REAGENTS [J].
BALD, E ;
SAIGO, K ;
MUKAIYAMA, T .
CHEMISTRY LETTERS, 1975, (11) :1163-1166
[5]   PALLADIUM(II) CATALYSED SYNTHESIS OF ALLYLIC ESTERS [J].
BRADY, DG .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1970, (07) :434-&
[6]  
Carruthers W., 2013, Cycloaddition reactions in organic synthesis
[7]   ACYCLIC STEREOCONTROL INDUCED BY ALLYLIC ALKOXY GROUPS - SYNTHETIC APPLICATIONS OF STEREOSELECTIVE DIHYDROXYLATION IN NATURAL PRODUCT SYNTHESIS [J].
CHA, JK ;
KIM, NS .
CHEMICAL REVIEWS, 1995, 95 (06) :1761-1795
[8]  
Ewin R. A., E EROS ENCY REAGENTS
[9]   The Claisen rearrangement. Response to solvents and substituents: The case for both hydrophobic and hydrogen bond acceleration in water and for a variable transition state [J].
Gajewski, JJ .
ACCOUNTS OF CHEMICAL RESEARCH, 1997, 30 (05) :219-225
[10]  
Godleski S.A., 1991, COMPREHENSIVE ORGANI, V4