The combination of domino process and kinetic resolution: Organocatalytic synthesis of functionalised cyclopentenes by sequential S N2′- Michael reaction

Lun Fu Yeh; Shaik Anwar; Kwunmin Chen

doi:10.1016/j.tet.2012.06.085

The combination of domino process and kinetic resolution: Organocatalytic synthesis of functionalised cyclopentenes by sequential S _N2′- Michael reaction

Lun Fu Yeh
, Shaik Anwar
, Kwunmin Chen^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

31 引文斯高帕斯（Scopus）

摘要

An interesting combination of organocatalytic cascade reaction and kinetic resolution was developed for the synthesis of functionalised cyclopentenes by sequential S _N2′-Michael process. Treatment of the racemic nitroallylic acetates with glutaraldehyde in the presence of diphenylprolinol silyl ether to give tetrasubstituted cyclopentenes with high to excellent stereoselectivities (up to 96% ee and 12:1 dr). The less reactive enantiomeric substrates were generally recovered with good to excellent optical purities (up to 99% ee).

原文	英語
頁（從 - 到）	7317-7321
頁數	5
期刊	Tetrahedron
卷	68
發行號	36
DOIs	https://doi.org/10.1016/j.tet.2012.06.085
出版狀態	已發佈 - 2012 9月 9

ASJC Scopus subject areas

生物化學
藥物發現
有機化學

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10.1016/j.tet.2012.06.085

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title = "The combination of domino process and kinetic resolution: Organocatalytic synthesis of functionalised cyclopentenes by sequential S N2′- Michael reaction",

abstract = "An interesting combination of organocatalytic cascade reaction and kinetic resolution was developed for the synthesis of functionalised cyclopentenes by sequential S N2′-Michael process. Treatment of the racemic nitroallylic acetates with glutaraldehyde in the presence of diphenylprolinol silyl ether to give tetrasubstituted cyclopentenes with high to excellent stereoselectivities (up to 96\% ee and 12:1 dr). The less reactive enantiomeric substrates were generally recovered with good to excellent optical purities (up to 99\% ee).",

keywords = "Cascade, Cyclopentene, Kinetic resolution, Michael reaction, Organocatalysis",

author = "Yeh, \{Lun Fu\} and Shaik Anwar and Kwunmin Chen",

note = "Funding Information: We thank the National Science Council of the Republic of China ( NSC 99-2113-M-003-002-MY3 and NSC 99-2119-M-003-001-MY2 ) and National Taiwan Normal University ( 100-D-06 ) for financial support of this work. ",

year = "2012",

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doi = "10.1016/j.tet.2012.06.085",

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T2 - Organocatalytic synthesis of functionalised cyclopentenes by sequential S N2′- Michael reaction

AU - Yeh, Lun Fu

AU - Anwar, Shaik

AU - Chen, Kwunmin

N1 - Funding Information: We thank the National Science Council of the Republic of China ( NSC 99-2113-M-003-002-MY3 and NSC 99-2119-M-003-001-MY2 ) and National Taiwan Normal University ( 100-D-06 ) for financial support of this work.

PY - 2012/9/9

Y1 - 2012/9/9

N2 - An interesting combination of organocatalytic cascade reaction and kinetic resolution was developed for the synthesis of functionalised cyclopentenes by sequential S N2′-Michael process. Treatment of the racemic nitroallylic acetates with glutaraldehyde in the presence of diphenylprolinol silyl ether to give tetrasubstituted cyclopentenes with high to excellent stereoselectivities (up to 96% ee and 12:1 dr). The less reactive enantiomeric substrates were generally recovered with good to excellent optical purities (up to 99% ee).

AB - An interesting combination of organocatalytic cascade reaction and kinetic resolution was developed for the synthesis of functionalised cyclopentenes by sequential S N2′-Michael process. Treatment of the racemic nitroallylic acetates with glutaraldehyde in the presence of diphenylprolinol silyl ether to give tetrasubstituted cyclopentenes with high to excellent stereoselectivities (up to 96% ee and 12:1 dr). The less reactive enantiomeric substrates were generally recovered with good to excellent optical purities (up to 99% ee).

KW - Cascade

KW - Cyclopentene

KW - Kinetic resolution

KW - Michael reaction

KW - Organocatalysis

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DO - 10.1016/j.tet.2012.06.085

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SN - 0040-4020

VL - 68

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JO - Tetrahedron

JF - Tetrahedron

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ER -

The combination of domino process and kinetic resolution: Organocatalytic synthesis of functionalised cyclopentenes by sequential S N2′- Michael reaction

摘要

ASJC Scopus subject areas

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The combination of domino process and kinetic resolution: Organocatalytic synthesis of functionalised cyclopentenes by sequential S _N2′- Michael reaction