Domino Michael/Oxa-Michael Reactions of the Unsymmetric Double Michael Acceptor for Access to Bicyclic Furo[2,3‑b]pyrrole

By creating an unsymmetric double Michael acceptor 1, we were able to synthesize the nonaromatic-fused bicyclic furo[2,3-b]pyrrole nucleus using a domino Michael/oxa-Michael reaction. Adopting benzoyl acetonitrile 2d (CN as the electron-withdrawing group) as a substrate, we discovered a (DHQ)2AQN-...

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Veröffentlicht in:	Journal of organic chemistry 2024-04, Vol.89 (8), p.5883-5895
Hauptverfasser:	Li, Hang, Wang, Ning, Zhou, Zhitin, Long, Lipeng, Li, Xun, Qian, Yiping, Qiao, Liang
Format:	Artikel
Sprache:	eng
Schlagworte:	acetonitrile antineoplastic activity density functional theory enantioselectivity organic chemistry pyrroles
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container_end_page	5895
container_issue	8
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container_title	Journal of organic chemistry
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creator	Li, Hang Wang, Ning Zhou, Zhitin Long, Lipeng Li, Xun Qian, Yiping Qiao, Liang
description	By creating an unsymmetric double Michael acceptor 1, we were able to synthesize the nonaromatic-fused bicyclic furo[2,3-b]pyrrole nucleus using a domino Michael/oxa-Michael reaction. Adopting benzoyl acetonitrile 2d (CN as the electron-withdrawing group) as a substrate, we discovered a (DHQ)2AQN-catalyzed method for high diastereo- and enantioselectivity of those products. The reaction path has been determined by isolating the reaction intermediates, and density functional theory calculations support these findings. Beyond providing a synthetic approach, this work illustrated the compounds’ possible use in antitumor activity.
doi_str_mv	10.1021/acs.joc.4c00161
format	Article
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Org. Chem</addtitle><date>2024-04-19</date><risdate>2024</risdate><volume>89</volume><issue>8</issue><spage>5883</spage><epage>5895</epage><pages>5883-5895</pages><issn>0022-3263</issn><issn>1520-6904</issn><eissn>1520-6904</eissn><abstract>By creating an unsymmetric double Michael acceptor 1, we were able to synthesize the nonaromatic-fused bicyclic furo[2,3-b]pyrrole nucleus using a domino Michael/oxa-Michael reaction. Adopting benzoyl acetonitrile 2d (CN as the electron-withdrawing group) as a substrate, we discovered a (DHQ)2AQN-catalyzed method for high diastereo- and enantioselectivity of those products. The reaction path has been determined by isolating the reaction intermediates, and density functional theory calculations support these findings. 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subjects	acetonitrile antineoplastic activity density functional theory enantioselectivity organic chemistry pyrroles
title	Domino Michael/Oxa-Michael Reactions of the Unsymmetric Double Michael Acceptor for Access to Bicyclic Furo[2,3‑b]pyrrole
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