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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.