Organocatalytic asymmetric Friedel-Crafts reaction of 1-naphthols with isatins: an enantioselective synthesis of 3-aryl-3-hydroxy-2-oxindoles

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• 作者：Jasneet Kaur ; Akshay Kumar ; Swapandeep Singh Chimni ; ^{sschimni@yahoo.com" class="auth_mail} ; ^{sschimni.chem@gndu.ac.in" class="auth_mail}
• 关键词：Organocatalysis ; Friedel&ndash ; Crafts reaction ; 3-Hydroxyoxindoles ; Cinchona-thioureas ; Isatins
• 刊名：Tetrahedron Letters
• 出版年：26 March, 2014
• 年：2014
• 卷：55
• 期：13
• 页码：2138-2141
• 全文大小：478 K

文摘

An organocatalytic enantioselective Friedel-Crafts reaction of 1-naphthols with isatins has been developed employing bifunctional thiourea-tertiary amine organocatalysts. A variety of isatin derivatives react well with 1-naphthols in the presence of Cinchona derived thiourea 1a to provide biologically important chiral 3-aryl-3-hydroxy-2-oxindoles (3a-zg) in good yield (70-84%) and moderate to good enantioselectivity (37-83%).