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

He Yu | Zendy; Liu Yue | Zendy; Liu Yu | Zendy; Kou XinXin | Zendy; Li QingZhu | Zendy; Li JiaHong | Zendy; Jiang HeZhong | Zendy; Leng HaiJun | Zendy; Peng Cheng | Zendy; Li JunLong | Zendy

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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.

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