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Stereoselective Construction of Complex Spirooxindoles via Bisthiourea Catalyzed Three‐Component Reactions
Author(s) -
Zhang LinLin,
Zhang JiWei,
Xiang ShaoHua,
Guo Zhen,
Tan Bin
Publication year - 2018
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201800368
Subject(s) - chemistry , aromatization , ene reaction , stereoselectivity , catalysis , component (thermodynamics) , multi component reaction , reactivity (psychology) , combinatorial chemistry , surface modification , reaction conditions , tandem , cascade reaction , organic chemistry , medicine , physics , alternative medicine , materials science , pathology , composite material , thermodynamics
A well‐designed three‐component reaction was developed to construct a class of optically active carbazolespirooxindole‐urazoles in good yields with excellent stereoselectivities via tandem Diels‐Alder reaction and ene‐reaction. The driving force originating from aromatization with in situ generated carbazolespirooxindole and the high reactivity of 4‐phenyl‐3 H ‐1,2,4‐triazole‐3,5‐dione facilitate the ene‐reaction in mild conditions. Control experiments indicated that the excellent stereoselectivities of ene‐reaction most likely came from the spatial configuration of the carbazolespirooxindole. The obtained products could be converted to other synthetic useful structures via diverse functionalization.