A bifunctional rosin-derived thiourea catalyzed asymmetric tandem reaction and its new mechanism

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• 作者：Hong-Rui Zhang ; Ji-Jun Xue ; Rui Chen ; Yu Tang ; ^{tangyu@lzu.edu.cn" class="auth_mail} ; Ying Li ; ^{liying@lzu.edu.cn" class="auth_mail}
• 关键词：Organocatalysis ; Diels&ndash ; Alder reaction ; Chiral thiourea ; Tandem reaction
• 刊名：Chinese Chemical Letters
• 出版年：May 2014
• 年：2014
• 卷：25
• 期：5
• 页码：710-714
• 全文大小：1116 K

文摘

A direct asymmetric tandem reaction of 伪-nitro ketones with 尾,纬-unsaturated 伪-ketoesters was found to be catalyzed by a bifunctional rosin-derived thiourea and gave 5-nitro-2-actoxyl-2-pentenates in excellent ee values and yields, a much better result than previously reported. Furthermore, through theoretical analysis, literature research and experimental verifications, a new mechanism involving an inverse-electron-demand Diels–Alder (IEDDAR) and a retro-Henry reaction was proposed.