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Highly Enantio- and Diastereoselective [4 + 2] Cycloaddition of 5H-oxazol-4-ones with N-Maleimides

Qiu, Shuai; Lee, Richmond; Zhu, Bo; Coote, Michelle; Zhao, Xiaowei; Jiang, Zhiyong


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.

CollectionsANU Research Publications
Date published: 2016
Type: Journal article
Source: The Journal of organic chemistry
DOI: 10.1021/acs.joc.6b01451
Access Rights: Open Access

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