Authors: Yin Xu, Qing Sun, Tong-De Tan, Ming-Yang Yang, Peng Yuan, Shao-Qi Wu, Xin Lu, Xin Hong, Long-Wu Ye

Abstract:

Described herein is an organocatalytic enantioselective desymmetrizingcycloisomerization of arylsulfonyl‐protected ynamide cyclohexanones, representing the first metal‐free asymmetric Conia‐ene‐type carbocyclization. This method allows the highly efficient and atom‐economical construction of a range of valuable morphans with wide substrate scope and excellent enantioselectivity (up to 97% ee). In addition, such a cycloisomerization of alkylsulfonyl‐protected ynamide cyclohexanones can lead to the divergent synthesis of normorphans as the main products with high enantioselectivity (up to 90% ee). Moreover, theoretical calculations are employed to elucidate the origins of regioselectivity and enantioselectivity.

Source: https://chem.xmu.edu.cn/en/info/1021/1745.htm

Full Link: https://onlinelibrary.wiley.com/doi/10.1002/anie.201908495