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

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

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

Author(s) -

Shuai Qiu,

Richmond Lee,

Bo Zhu,

Michelle L. Coote,

Xiaowei Zhao,

Zhiyong Jiang

Publication year - 2016

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.6b01451

Subject(s) - chemistry , cycloaddition , stereochemistry , organic chemistry , catalysis

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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