Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 360, Issue 7, Pages 1499-1509Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201800009
Keywords
organic catalysis; conjugate addition; Phase Transfer Catalysis; isoxazolidinone; Meldrum's acid
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Funding
- INSA Rouen, Rouen University, CNRS
- EFRD
- Labex SynOrg [ANR-11-LABX-0029]
- region Normandie (CRUNCh network)
- ENSICAEN
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An efficient enantioselective Michael reaction of readily available -substituted N-Boc isoxazolidin-5-ones is described under phase transfer conditions with up to 95:5 er. The organocatalytic process is promoted by a low catalytic loading of a commercially available N-spiro quaternary ammonium salt. This sequence opens an entry to chiral heterocyclic platforms displaying a -amino carbonyl motif with an -all-carbon quaternary stereogenic center. The methodology was also successfully extended to the asymmetric amination reaction using an azodicarboxylate electrophile.
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