Stereoselective synthesis of spirocyclohexadiene-pyrazolones via organic base and/or hydrogen bonding assisted [3 + 3] annulation reactions

We have reported the 1,4-diazabicyclo[2.2.2]octane (DABCO)-catalyzed [3 + 3] cycloaddition reaction of α-arylidene pyrazolinones and 2-benzylidenemalononitriles under mild reaction conditions, which afforded the spirocyclohexadiene-pyrazolones in good yields with moderate to good diastereoselectivit...

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Veröffentlicht in:	Organic Chemistry Frontiers 2019-06, Vol.6 (11), p.1842-1857
Hauptverfasser:	Sun, Bing-Bing, Zhang, Jun-Qi, Chen, Jun-Bo, Fan, Wei-Tai, Yu, Jie-Qiang, Hu, Jia-Ming, Wang, Xing-Wang
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Sprache:	eng
Schlagworte:	Chemical reactions Crystallography Cycloaddition Hydrogen bonding Optical activity Organic chemistry Pyrazolones Stereoselectivity
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creator	Sun, Bing-Bing Zhang, Jun-Qi Chen, Jun-Bo Fan, Wei-Tai Yu, Jie-Qiang Hu, Jia-Ming Wang, Xing-Wang
description	We have reported the 1,4-diazabicyclo[2.2.2]octane (DABCO)-catalyzed [3 + 3] cycloaddition reaction of α-arylidene pyrazolinones and 2-benzylidenemalononitriles under mild reaction conditions, which afforded the spirocyclohexadiene-pyrazolones in good yields with moderate to good diastereoselectivities. By the use of a cinchona alkaloid derived bifunctional squaramide-tertiary amine catalyst, an asymmetric variant of this [3 + 3] cycloaddition reaction has also been developed to provide optically active spirocyclohexadiene-pyrazolones bearing an all-carbon quaternary chiral center in good yields with excellent enantioselectivities and moderate diastereoselectivities.
doi_str_mv	10.1039/C8QO01391H
format	Article
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source	Royal Society Of Chemistry Journals 2008-
subjects	Chemical reactions Crystallography Cycloaddition Hydrogen bonding Optical activity Organic chemistry Pyrazolones Stereoselectivity
title	Stereoselective synthesis of spirocyclohexadiene-pyrazolones via organic base and/or hydrogen bonding assisted [3 + 3] annulation reactions
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