Abstract
An organocatalytic asymmetric reaction between 5H-oxazol-4-ones and N-substituted maleimides is disclosed. Employing Takemoto's chiral tertiary amine-thiourea as the catalyst, [4 + 2] annulation reactions were performed with high chemoselectivity, leading to a series of biologically important chiral oxo-bridged piperidone-fused succinimides in good to excellent enantioselectivities (up to >99% ee) and >19:1 dr.
Original language | English |
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Pages (from-to) | 8061-8069 |
Number of pages | 9 |
Journal | Journal of Organic Chemistry |
Volume | 81 |
Issue number | 17 |
DOIs | |
Publication status | Published - 2 Sept 2016 |
Externally published | Yes |
Bibliographical note
Funding Information:We are grateful for the grants from NSFC (21072044) and Henan province (14IRTSTHN006, 152300410057, 162300410002).
Publisher Copyright:
© 2016 American Chemical Society.
Keywords
- Enantio
- Diastereoselective
- Cycloaddition
- N-Maleimides
- allylic
- alkylation
- chiral
- molecules