乙烯基磺酰胺的热及高压分子内狄尔斯-阿尔德反应
Thermal and high pressure intramolecular Diels-Alder reaction of vinylsulfonamides.
作者信息
Rogachev Victor O, Metz Peter
机构信息
Department of Organic Chemistry, Tomsk Polytechnic University, Prospekt Lenina 30, 634050 Tomsk, Russia.
出版信息
Nat Protoc. 2006;1(6):3076-87. doi: 10.1038/nprot.2006.463.
Vinylsulfonamides with a furan, carbocyclic, semicyclic or acyclic 1,3-diene moiety are synthetized via a domino elimination-amidation reaction of 2-chloroethanesulfonyl chloride. Intramolecular Diels-Alder reaction of these vinylsulfonamides with thermal (toluene, 110 degrees C) or high pressure (dichloromethane, 13 kbar) activation provides efficient access to a range of gamma- and delta-sultams following a 2-3 d long synthetic procedure. Enantiopure sultams are readily obtained from N-1-phenylethyl substituted vinylsulfonamides.
具有呋喃、碳环、半环或无环1,3 - 二烯部分的乙烯基磺酰胺是通过2 - 氯乙烷磺酰氯的多米诺消除 - 酰胺化反应合成的。这些乙烯基磺酰胺在热（甲苯，110摄氏度）或高压（二氯甲烷，13千巴）活化下进行分子内狄尔斯 - 阿尔德反应，经过2 - 3天的合成过程，能够高效地合成一系列γ - 和δ - 磺内酰胺。对映体纯的磺内酰胺很容易从N - 1 - 苯乙基取代的乙烯基磺酰胺中获得。
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