A Highly Enantioselective Approach to Hydrocarbazole Derivatives Catalyzed by Diphenylmethylidene Bis(oxazoline)‐Ni(II) Complexes | Zendy

Luo Jiayu | Zendy; Chenzhang Pengfei | Zendy; Lan Wenjie | Zendy; Li Jiaqi | Zendy; Qin Zhaohai | Zendy; Fu Bin | Zendy

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A Highly Enantioselective Approach to Hydrocarbazole Derivatives Catalyzed by Diphenylmethylidene Bis(oxazoline)‐Ni(II) Complexes

Author(s) -

Luo Jiayu,

Chenzhang Pengfei,

Lan Wenjie,

Li Jiaqi,

Qin Zhaohai,

Fu Bin

Publication year - 2021

Publication title -

chemistryselect

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.437

H-Index - 34

ISSN - 2365-6549

DOI - 10.1002/slct.202102134

Subject(s) - enantioselective synthesis , oxazoline , stereocenter , yield (engineering) , catalysis , chemistry , cycloaddition , optically active , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , materials science , metallurgy

The first Ni(II)‐catalyzed asymmetric [4+2] cycloaddition of silyloxyvinylindoles with 2‐enoyl pyridines was successfully accomplished by using a diphenylmethylidene‐tethered bis(oxazoline). A series of optically active hydrocarbazole derivatives with three contiguous stereocenters were achieved in good yield with both high diastereo‐(>20 : 1) and enantioeselectivities (up to 97 % ee) under mild conditions. Moreover, various 2‐enoyl azaarenes were compatible with the reaction. A proposed mechanism was deducted.

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