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Diastereo‐ and Enantioselective Synthesis of Chiral Pyrrolidine‐Fused Spirooxindoles via Organocatalytic [3+2] 1,3‐Dipolar Cycloaddition of Azomethine Ylides with Maleimides
Author(s) -
Zhao HongWu,
Yang Zhao,
Meng Wei,
Tian Ting,
Li Bo,
Song XiuQing,
Chen XiaoQin,
Pang HaiLiang
Publication year - 2015
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.201500162
Subject(s) - chemistry , enantioselective synthesis , pyrrolidine , azomethine ylide , cycloaddition , isatin , pyrrole , squaramide , indoline , 1,3 dipolar cycloaddition , cinchona , organocatalysis , stereochemistry , organic chemistry , catalysis
In the presence of a Cinchona alkaloid‐based squaramide organocatalyst, the [3+2] cycloaddition of isatin‐derived azomethine ylides with maleimides proceeded readily, thus delivering the desired pyrrolidine‐fused spirooxindoles in 61–89% yields with >20:1 dr and 12 to >99 % ee . The absolute configuration of 5‐chloro‐1,5′‐dimethyl‐3′‐phenyl‐3′,3a′‐dihydro‐2′ H ‐spiro[indoline‐3,1′‐pyrrolo[3,4‐ c ]pyrrole]‐2,4′,6′(5′ H ,6a′ H )‐trione was unambiguously determined by means of X‐ray single crystal structure analysis. The reaction mechanism was hypothesized to account for the enantioselective formation of 5‐chloro‐1,5′‐dimethyl‐3′‐phenyl‐3′,3a′‐dihydro‐2′ H ‐spiro[indoline‐3,1′‐pyrrolo[3,4‐ c ]pyrrole]‐2,4′,6′(5′ H ,6a′ H )‐trione.