Diastereodivergent Formal 1,3‐Dipolar Cycloaddition of 5‐alkenyl thiazolones to Access Stereochemically Diverse Pyrrolidinyl Spirooxindoles

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 sp...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2020-05, Vol.362 (10), p.2052-2058
Main Authors: He, Yu, Liu, Yue, Liu, Yu, Kou, Xin‐Xin, Li, Qing‐Zhu, Li, Jia‐Hong, Jiang, He‐Zhong, Leng, Hai‐Jun, Peng, Cheng, Li, Jun‐Long
Format: Article
Language:English
Subjects:
1,3-dipolar cycloaddition
Cycloaddition
diastereodivergent synthesis
Imines
multiple diastereoisomers
organocatalysis
spirooxindoles
Stereoselectivity
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Summary: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201901541