Diastereoselective Synthesis of Indolindiones by Formal [5+1] Double Michael Cycloaddition to 4-Cinnamoylpyrrolediones

An efficient [5+1] double Michael cycloaddition of enolates to 4‐cinnamoylpyrrole‐2,3‐diones was investigated; the reaction allows for the highly diastereoselective assembly of indoline scaffolds with up to three contiguous stereogenic centers. An efficient [5+1] double Michael cycloaddition (DMCA)...

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Bibliographic Details
Published in:European journal of organic chemistry 2015-04, Vol.2015 (12), p.2739-2744
Main Authors: Silaichev, Pavel S., Filimonov, Valeriy O., Slepukhin, Pavel A., Rubin, Michael, Maslivets, Andrey N.
Format: Article
Language:English
Subjects:
Cycloaddition
Diastereoselectivity
Lactams
Michael addition
Nitrogen heterocycles
Synthetic methods
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Summary:An efficient [5+1] double Michael cycloaddition of enolates to 4‐cinnamoylpyrrole‐2,3‐diones was investigated; the reaction allows for the highly diastereoselective assembly of indoline scaffolds with up to three contiguous stereogenic centers. An efficient [5+1] double Michael cycloaddition (DMCA) of enolates to 4‐cinnamoylpyrrole‐2,3‐diones is demonstrated; the reaction allows for the highly diastereoselective assembly of indoline scaffolds with up to three contiguous stereogenic centers.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201500141