A chiral cobalt() complex catalyzed enantioselective aza-Piancatelli rearrangement/Diels-Alder cascade reaction

A chiral N , N ′-dioxide/cobalt( ii ) complex catalyzed highly diastereoselective and enantioselective tandem aza-Piancatelli rearrangement/intramolecular Diels-Alder reaction has been disclosed. Various valuable hexahydro-2 a ,5-epoxycyclopenta[ cd ]isoindoles bearing six contiguous stereocenters h...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2020-04, Vol.11 (15), p.3862-3867
Main Authors: Shen, Bin, He, Qianwen, Dong, Shunxi, Liu, Xiaohua, Feng, Xiaoming
Format: Article
Language:English
Subjects:
Aniline
Cascade chemical reactions
Chemistry
Cobalt compounds
Crystallography
Enantiomers
NMR
Nuclear magnetic resonance
Stereoselectivity
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Summary:A chiral N , N ′-dioxide/cobalt( ii ) complex catalyzed highly diastereoselective and enantioselective tandem aza-Piancatelli rearrangement/intramolecular Diels-Alder reaction has been disclosed. Various valuable hexahydro-2 a ,5-epoxycyclopenta[ cd ]isoindoles bearing six contiguous stereocenters have been obtained in good yields with excellent diastereo- and enantio-selectivities from a wide range of both readily available 2-furylcarbinols and N -(furan-2-ylmethyl)anilines. An asymmetric aza-Piancatelli rearrangement/Diels-Alder cascade reaction between 2-furylcarbinols and N -(furan-2-ylmethyl)anilines was realized by using a chiral N , N ′-dioxide/cobalt( ii ) complex catalyst.
ISSN:2041-6520
2041-6539
DOI:10.1039/d0sc00542h