[Angew. Chem. Int. Ed.] Prof. Longwu Ye and Prof. Xin Lu’ s groups published a paper entitled “Organocatalytic Enantioselective Conia-Ene-Type Carbocyclization of Ynamide-Cyclohexanones: Regiodivergent Synthesis of Morphans and Normorphans”-College of Chemistry and Chemical Engineering

[Angew. Chem. Int. Ed.] Prof. Longwu Ye and Prof. Xin Lu’ s groups published a paper entitled “Organocatalytic Enantioselective Conia-Ene-Type Carbocyclization of Ynamide-Cyclohexanones: Regiodivergent Synthesis of Morphans and Normorphans”

Publish Date:01.February 2020 Visted: Times

Title: Organocatalytic Enantioselective Conia-Ene-Type Carbocyclization of Ynamide-Cyclohexanones: Regiodivergent Synthesis of Morphans and Normorphans

Angew. Chem. Int. Ed., 2019, 58, 16252-16259

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.

Published: 24August 2019

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

Research Highlights

[Angew. Chem. Int. Ed.] Prof. Longwu Ye and Prof. Xin Lu’ s groups published a paper entitled “Organocatalytic Enantioselective Conia-Ene-Type Carbocyclization of Ynamide-Cyclohexanones: Regiodivergent Synthesis of Morphans and Normorphans”