Intramolecular [2+2] Cycloaddition Reactions of Alkynyl Ether Derived Ketenes. A Convenient Synthesis of Donor-Acceptor Cyclobutanes

被引：20
|
作者：
Tran, Vincent [1 ]
Minehan, Thomas G. [1 ]
机构：
[1] Calif State Univ Northridge, Dept Chem & Biochem, Northridge, CA 91330 USA
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 24期
基金：
美国国家卫生研究院;
关键词：
ACETYLENIC ETHERS; EFFICIENT SYNTHESIS; 3-ETHOXYCYCLOBUTANONES; REARRANGEMENT; DERIVATIVES; ALDEHYDES; CHEMISTRY; ALKENES; KETONES; ALLYL;
D O I：
10.1021/ol202989c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Mild thermolysis of tert-butyl alkynyl ethers furnishes aldoketenes, which undergo facile [2 + 2] cycloaddition reactions with pendant di- and trisubstituted alkenes. A wide variety of cis-fused cyclobutanones are produced in moderate to high diastereoselectivity and good to excellent yields by this method, and free hydroxyl groups are tolerated in the ene-ynol ether starting materials. Enol-ynol ethers also undergo efficient reaction to produce donor acceptor cyclobutanes in high yields.
引用
收藏
页码：6588 / 6591
页数：4
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