Facile Domino Access to Chiral Bicyclo[3.2.1]octanes and Discovery of a New Catalytic Activation Mode

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• 作者：Bin Tan ; Yunpeng Lu ; Xiaofei Zeng ; Pei Juan Chua ; Guofu Zhong
• 刊名：Organic Letters
• 出版年：2010
• 出版时间：June 18, 2010
• 年：2010
• 卷：12
• 期：12
• 页码：2682-2685
• 全文大小：189K
• 年卷期：v.12,no.12(June 18, 2010)
• ISSN：1523-7052

文摘

A highly enantio- and diastereoselective organocatalytic domino Michael−Henry process for the preparation of synthetically unique and medicinally important bicyclo[3.2.1]octane derivatives with four stereogenic centers including two quaternary stereocenters has been developed. Theoretical DFT calculations on the transition states have been carried out to reveal origins of the excellent stereoselectivities. A novel dual model was thus proposed.