一种由森田-贝利斯-希尔曼碳酸酯简便温和地合成三取代烯丙基砜的方法。

A facile and mild synthesis of trisubstituted allylic sulfones from Morita-Baylis-Hillman carbonates.

作者信息

Jiang Lin, Li Yong-Gen, Zhou Jiang-Feng, Chuan Yong-Ming, Li Hong-Li, Yuan Ming-Long

机构信息

Engineering Research Center of Biopolymer Functional Materials of Yunnan, School of Chemistry and Biotechnology, Yunnan Minzu University, Kunming 650500, China.

Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, School of Chemistry and Biotechnology, Yunnan Minzu University, Kunming 650500, China.

出版信息

Molecules. 2015 May 7;20(5):8213-22. doi: 10.3390/molecules20058213.

DOI:10.3390/molecules20058213

PMID:25961162

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6272667/

Abstract

An efficient and catalyst-free synthesis of trisubstituted allylic sulfones through an allylic sulfonylation reaction of Morita-Baylis-Hillman (MBH) carbonates with sodium sulfinates has been developed. Under the optimized reaction conditions, a series of trisubstituted allylic sulfones were rapidly prepared in good to excellent yields (71%-99%) with good to high selectivity (Z/E from 79:21 to >99:1). Compared with known synthetic methods, the current protocol features mild reaction temperature, high efficiency and easily available reagents.

摘要

通过森田-贝利斯-希尔曼（MBH）碳酸酯与亚磺酸钠的烯丙基磺酰化反应，开发了一种高效且无催化剂的三取代烯丙基砜的合成方法。在优化的反应条件下，一系列三取代烯丙基砜能快速制备出来，产率良好至优异（71%-99%），选择性良好至高（Z/E从79:21到>99:1）。与已知的合成方法相比，该方法具有反应温度温和、效率高和试剂易于获得的特点。