Asymmetric Synthesis of Chiral Dihydrothiopyrans via an Organocatalytic Enantioselective Formal Thio [3 + 3] Cycloaddition Reaction with Binucleophilic Bisketone Thioethers

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• 作者：Shengzheng Wang ; Yongqiang Zhang ; Guoqiang Dong ; Shanchao Wu ; Shiping Zhu ; Zhenyuan Miao ; Jianzhong Yao ; Hao Li ; Jian Li ; Wannian Zhang ; Chunquan Sheng ; Wei Wang
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：November 1, 2013
• 年：2013
• 卷：15
• 期：21
• 页码：5570-5573
• 全文大小：245K
• 年卷期：v.15,no.21(November 1, 2013)
• ISSN：1523-7052

文摘

An unprecedented organocatalytic highly enantioselective approach to a 3,4-dihydro-2H-thiopyran scaffold with two contiguous stereogenic centers has been implemented through a formal thio [3 + 3] cycloaddition process involving a Michael鈥揳ldol condensation cascade sequence. Notably, a new class of binucleophilic bisketone thioethers is designed for the process. Furthermore, the fine-tuning of their reactivity enables the cascade process to proceed with highly regioselectively.