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Diastereodivergent Formal 1,3‐Dipolar Cycloaddition of 5‐alkenyl thiazolones to Access Stereochemically Diverse Pyrrolidinyl Spirooxindoles
Author(s) -
He Yu,
Liu Yue,
Liu Yu,
Kou XinXin,
Li QingZhu,
Li JiaHong,
Jiang HeZhong,
Leng HaiJun,
Peng Cheng,
Li JunLong
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901541
Subject(s) - chemistry , diastereomer , stereoselectivity , organocatalysis , yield (engineering) , stereochemistry , cycloaddition , enantioselective synthesis , transformation (genetics) , combinatorial chemistry , catalysis , organic chemistry , gene , biochemistry , materials science , metallurgy
We report here a stereoselective [3+2] cyclization of 5‐alkenyl thiazolones and ketimines that allows the assembly of three diastereoisomers through the combination of stereodivergent organocatalysis and the following diastereoselective transformation of products. A broad spectrum of pyrrolidinyl spirooxindoles featuring stereochemical diversity has been synthesized through organocatalytic formal 1,3‐dipolar cycloadditions with up to 98% yield, >20:1 dr and 99:1 er.