Chiral Binaphthyl Box-Copper-Catalyzed Enantioselective Tandem Michael–Ketalization Annulations for Optically Active Aryl and Heteroaryl Fused Bicyclicnonanes

The combination of chiral binaphthyl box-copper­(II) with triflimide (Tf2NH) was identified as an efficient catalytic system for the asymmetric Michael/ketalization of (E)-2-hydroxyaryl-2-oxobut-3-enoates or (E)-ethyl 4-(2-aminoaryl)-2-oxobut-3-enoates with pyrazolone derivatives. The corresponding...

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Published inOrganic letters Vol. 22; no. 10; pp. 3936 - 3941
Main Authors Fan, Wei-Tai, Yang, Xiao-Peng, Lv, Hao-Peng, Wang, Xing-Wang, Wang, Zheng
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.05.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ASYMMETRIC-SYNTHESIS
FACILE SYNTHESIS
ACID
PROANTHOCYANIDINS
PYRAZOLINE
A-TYPE
INHIBITORS
IDENTIFICATION
DERIVATIVES
SPIROKETALS
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Summary:The combination of chiral binaphthyl box-copper­(II) with triflimide (Tf2NH) was identified as an efficient catalytic system for the asymmetric Michael/ketalization of (E)-2-hydroxyaryl-2-oxobut-3-enoates or (E)-ethyl 4-(2-aminoaryl)-2-oxobut-3-enoates with pyrazolone derivatives. The corresponding asymmetric tandem reactions provided a series of enantioenriched aryl and heteroaryl fused 2,8-O,O- or O,N-bicyclo­[3.3.1]­nonanes in high yields with excellent enantio- and diastereoselectivities.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01221