微波辅助三丙炔基乙烯基醚的 C2-链官能化呋喃的级联反应。

Microwave-assisted domino access to C2-chain functionalized furans from tertiary propargyl vinyl ethers.

机构信息

Departamento de Química Biológica y Biotecnología, Instituto de Productos Naturales y Agrobiología , CSIC, Astrofísico Francisco Sánchez 3, 38206 La Laguna, Tenerife, Spain.

出版信息

Org Lett. 2011 Aug 19;13(16):4422-5. doi: 10.1021/ol2017609. Epub 2011 Jul 22.

DOI:10.1021/ol2017609

PMID:21780753

Abstract

Tertiary propargyl vinyl ethers armed with an electron-withdrawing group (amide or ester) at the tertiary propargylic position have been efficiently transformed into trisubstituted C(2)-chain functionalized furans. The metal-free domino transformation involves a microwave-assisted tandem [3,3]-propargyl Claisen rearrangement/5-exo-dig O-cyclization reaction. The manifold can be performed in a one-pot fashion from the primary components (1,2-ketoester/1,2-ketoamide or tertiary propargyl alcohols).

摘要

三级炔丙基乙烯基醚在三级炔丙位上带有吸电子基团（酰胺或酯），已被有效地转化为三取代的 C(2)-链官能化呋喃。该无金属的串联转化涉及微波辅助的[3,3]-炔丙基 Claisen 重排/5-endo-dig O-环化反应。该多组分反应可以从起始原料（1,2-酮酯/1,2-酮酰胺或三级炔丙醇）一锅法进行。