Highly Enantio- and Diastereoselective [4 + 2] Cycloaddition of 5H-oxazol-4-ones with N-Maleimides
Date
2016
Authors
Qiu, Shuai
Lee, Richmond
Zhu, Bo
Coote, Michelle
Zhao, Xiaowei
Jiang, Zhiyong
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Volume Title
Publisher
American Chemical Society
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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Source
The Journal of organic chemistry
Type
Journal article
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Access Statement
Open Access