Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2017, Issue 16, Pages 2245-2257Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201700031
Keywords
Isocyanides; Multicomponent reactions; Nitrogen heterocycles; Cyclization; Small ring systems; Lactams
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Funding
- Council of Scientific and Industrial Research (CSIR), New Delhi under the 12th Five Year Plan Project [BSC0102]
- Science and Engineering Research Board (SERB) under the Fast Track Research Grant for the Young Scientists [SB/FT/CS-071/2014]
- CSIR, New Delhi
- University Grants Commission (UGC), New Delhi
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A series of ethanolamine-derived Ugi four-component-reaction adducts were subjected to a base-mediated cycloisomerization/rearrangement cascade to give functionalized 2,5-pyrrolidinediones in good-to-excellent yields. The method was extended to amino-acid-derived chiral ethanolamines to access enantiomerically pure 2,5-pyrrolidinediones. The reaction is diastereospecific, and mixtures of 2,5-pyrrolidinediones and -lactams were formed with high enantiomeric excess. Mechanistic studies revealed that the reaction proceeds through the formation of a -lactam intermediate by intramolecular cyclization in a 4-exo-dig fashion. This then rearranges further to give the 2,5-pyrrolidinedione with the help of the hydroxyethyl appendage. Computational analysis of the reaction profile demonstrated that the intramolecular 4-exo-dig cyclization is energetically favoured over the 5-endo-dig pathway, so this results in the formation of the beta-lactam.
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