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

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

doi:10.1021/acs.joc.6b01451

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

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

20 Citations (Scopus)

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
Pages (from-to)	8061-8069
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	81
Issue number	17
DOIs	https://doi.org/10.1021/acs.joc.6b01451
Publication status	Published - 2 Sept 2016

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

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.",

author = "Shuai Qiu and Richmond Lee and Bo Zhu and Coote, {Michelle L.} and Xiaowei Zhao and Zhiyong Jiang",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

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doi = "10.1021/acs.joc.6b01451",

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T1 - Highly Enantio- and Diastereoselective [4 + 2] Cycloaddition of 5H-oxazol-4-ones with N-Maleimides

AU - Qiu, Shuai

AU - Lee, Richmond

AU - Zhu, Bo

AU - Coote, Michelle L.

AU - Zhao, Xiaowei

AU - Jiang, Zhiyong

PY - 2016/9/2

Y1 - 2016/9/2

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84984878630&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.6b01451

DO - 10.1021/acs.joc.6b01451

M3 - Article

SN - 0022-3263

VL - 81

SP - 8061

EP - 8069

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 17

ER -

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

Abstract

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