Asymmetric Organocatalytic Synthesis of Highly Substituted Cyclohexenols by Domino Double-Michael Reactions of 1-Hydroxy-1,4-dien-3-ones and 2-Alkylidenemalononitriles

Yeong Jiunn Jang; Yu Shan Chen; Chia Jui Lee; Chi Han Chen; Ganapuram Madhusudhan Reddy; Chi Ting Ko; Wenwei Lin

doi:10.1002/ejoc.201403677

Asymmetric Organocatalytic Synthesis of Highly Substituted Cyclohexenols by Domino Double-Michael Reactions of 1-Hydroxy-1,4-dien-3-ones and 2-Alkylidenemalononitriles

Yeong Jiunn Jang, Yu Shan Chen, Chia Jui Lee, Chi Han Chen, Ganapuram Madhusudhan Reddy, Chi Ting Ko, Wenwei Lin^*

^*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

12 引文斯高帕斯（Scopus）

摘要

A facile asymmetric synthetic protocol to afford 2,6-disubstituted 4-hydroxy-3-oxocyclohex-3-ene-1,1-dicarbonitriles has been developed through the domino double-Michael addition of 1,5-disubstituted 1-hydroxy-1,4-dien-3-ones to 2-alkylidenemalononitriles using quinine as the catalyst. This simple organocatalytic domino process provides access to various highly functionalized chiral 4-hydroxy-3-oxocyclohex-3-enes, which are the rarely reported chiral diketo cyclohexane analogues, in moderate-to-good yields and enantioselectivities and with excellent diastereoselectivities (>25:1 dr).

原文	英語
頁（從 - 到）	2066-2074
頁數	9
期刊	European Journal of Organic Chemistry
卷	2015
發行號	9
DOIs	https://doi.org/10.1002/ejoc.201403677
出版狀態	已發佈 - 2015 3月

ASJC Scopus subject areas

物理與理論化學
有機化學

存取文件

10.1002/ejoc.201403677

其它文件與鏈接

CCDC 940048: Experimental Crystal Structure Determination
Jang, Y. (Contributor), Chen, Y. (Contributor), Lee, C. (Contributor), Chen, C. (Contributor), Reddy, G. M. (Contributor), Ko, C. (Contributor) & Lin, W. (Contributor), Unknown Publisher, 2014
DOI: 10.5517/cc10k64x, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc10k64x&sid=DataCite
資料集: Dataset

引用此

Asymmetric Organocatalytic Synthesis of Highly Substituted Cyclohexenols by Domino Double-Michael Reactions of 1-Hydroxy-1,4-dien-3-ones and 2-Alkylidenemalononitriles. / Jang, Yeong Jiunn; Chen, Yu Shan; Lee, Chia Jui 等.
於: European Journal of Organic Chemistry, 卷 2015, 編號 9, 03.2015, p. 2066-2074.

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

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title = "Asymmetric Organocatalytic Synthesis of Highly Substituted Cyclohexenols by Domino Double-Michael Reactions of 1-Hydroxy-1,4-dien-3-ones and 2-Alkylidenemalononitriles",

abstract = "A facile asymmetric synthetic protocol to afford 2,6-disubstituted 4-hydroxy-3-oxocyclohex-3-ene-1,1-dicarbonitriles has been developed through the domino double-Michael addition of 1,5-disubstituted 1-hydroxy-1,4-dien-3-ones to 2-alkylidenemalononitriles using quinine as the catalyst. This simple organocatalytic domino process provides access to various highly functionalized chiral 4-hydroxy-3-oxocyclohex-3-enes, which are the rarely reported chiral diketo cyclohexane analogues, in moderate-to-good yields and enantioselectivities and with excellent diastereoselectivities (>25:1 dr).",

keywords = "Alkaloids, Carbocycles, Domino reactions, Enones, Michael addition, Organocatalysis",

author = "Jang, {Yeong Jiunn} and Chen, {Yu Shan} and Lee, {Chia Jui} and Chen, {Chi Han} and Reddy, {Ganapuram Madhusudhan} and Ko, {Chi Ting} and Wenwei Lin",

note = "Publisher Copyright: {\textcopyright} 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2015",

month = mar,

doi = "10.1002/ejoc.201403677",

language = "English",

volume = "2015",

pages = "2066--2074",

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T1 - Asymmetric Organocatalytic Synthesis of Highly Substituted Cyclohexenols by Domino Double-Michael Reactions of 1-Hydroxy-1,4-dien-3-ones and 2-Alkylidenemalononitriles

AU - Jang, Yeong Jiunn

AU - Chen, Yu Shan

AU - Lee, Chia Jui

AU - Chen, Chi Han

AU - Reddy, Ganapuram Madhusudhan

AU - Ko, Chi Ting

AU - Lin, Wenwei

PY - 2015/3

Y1 - 2015/3

N2 - A facile asymmetric synthetic protocol to afford 2,6-disubstituted 4-hydroxy-3-oxocyclohex-3-ene-1,1-dicarbonitriles has been developed through the domino double-Michael addition of 1,5-disubstituted 1-hydroxy-1,4-dien-3-ones to 2-alkylidenemalononitriles using quinine as the catalyst. This simple organocatalytic domino process provides access to various highly functionalized chiral 4-hydroxy-3-oxocyclohex-3-enes, which are the rarely reported chiral diketo cyclohexane analogues, in moderate-to-good yields and enantioselectivities and with excellent diastereoselectivities (>25:1 dr).

AB - A facile asymmetric synthetic protocol to afford 2,6-disubstituted 4-hydroxy-3-oxocyclohex-3-ene-1,1-dicarbonitriles has been developed through the domino double-Michael addition of 1,5-disubstituted 1-hydroxy-1,4-dien-3-ones to 2-alkylidenemalononitriles using quinine as the catalyst. This simple organocatalytic domino process provides access to various highly functionalized chiral 4-hydroxy-3-oxocyclohex-3-enes, which are the rarely reported chiral diketo cyclohexane analogues, in moderate-to-good yields and enantioselectivities and with excellent diastereoselectivities (>25:1 dr).

KW - Alkaloids

KW - Carbocycles

KW - Domino reactions

KW - Enones

KW - Michael addition

KW - Organocatalysis

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U2 - 10.1002/ejoc.201403677

DO - 10.1002/ejoc.201403677

M3 - Article

AN - SCOPUS:85027935988

SN - 1434-193X

VL - 2015

SP - 2066

EP - 2074

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 9

ER -

Asymmetric Organocatalytic Synthesis of Highly Substituted Cyclohexenols by Domino Double-Michael Reactions of 1-Hydroxy-1,4-dien-3-ones and 2-Alkylidenemalononitriles

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 940048: Experimental Crystal Structure Determination

引用此