Asymmetric Formal Vinylogous Iminium Ion Activation for Vinyl-Substituted Heteroaryl and Aryl Aldehydes

The vinyl group tethered to furfurals could be LUMO-lowered by forming formal vinylogous iminium ion intermediates catalyzed by a chiral secondary amine and underwent asymmetric [3 + 2] cycloaddition reactions with N-trifluoroethyl-substituted isatin imines, furnishing a variety of spirooxindoles in...

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Published inOrganic letters Vol. 21; no. 23; pp. 9628 - 9632
Main Authors Gao, Xin-Yue, Yan, Ru-Jie, Xiao, Ben-Xian, Du, Wei, Albrecht, Łukasz, Chen, Ying-Chun
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.12.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
NITRONES
DIELS-ALDER REACTION
1,3-DIPOLAR CYCLOADDITION
CONSTRUCTION
TRIENAMINE
3-FURFURAL DERIVATIVES
3+2 CYCLOADDITION
N-2,2,2-TRIFLUOROETHYLISATIN KETIMINES
MICHAEL ADDITION
SPIROOXINDOLES
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Summary:The vinyl group tethered to furfurals could be LUMO-lowered by forming formal vinylogous iminium ion intermediates catalyzed by a chiral secondary amine and underwent asymmetric [3 + 2] cycloaddition reactions with N-trifluoroethyl-substituted isatin imines, furnishing a variety of spirooxindoles incorporating a 3,2′-pyrrolidine motif with excellent stereoselectivity. In addition, this strategy has been successfully expanded to a number of vinyl-substituted electron-rich heteroaryl aldehydes and even some specific aryl aldehydes.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03794