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

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

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

Date

2016-09-02

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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.

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https://dspace-test.anu.edu.au/handle/1885/733756412

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DevOps Pure Testing

Source

Journal of Organic Chemistry

Type

Article

DOI

10.1021/acs.joc.6b01451

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

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