Copper-Catalyzed Cascade Reaction via Intramolecular Hydroamination Cyclization of Homopropargylic Amines and Intermolecular Povarov Reaction with Imines

A new one-pot cascade reaction of homopropargylic amines with simple imines is developed in the presence of Cu­(OTf)2 and affords a series of hexahydro-1H-pyrrolo­[3,2-c]­quinoline derivatives in good to high yields. This reaction proceeds through an intramolecular hydroamination cyclization of homo...

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Published inOrganic letters Vol. 18; no. 10; pp. 2367 - 2370
Main Authors Wang, Hongkai, Wang, Chan, Huang, Kaimeng, Liu, Lingyan, Chang, Weixing, Li, Jing
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.05.2016
Amer Chemical Soc
Subjects
amines
chemical bonding
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
copper
imines
Physical Sciences
quinoline
Science & Technology
2-(1-ALKYNYL)-2-ALKEN-1-ONES
ACID
ENANTIOSELECTIVE SYNTHESIS
PYRROLES
ALKYNES
DERIVATIVES
HIGHLY SUBSTITUTED FURANS
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Summary:A new one-pot cascade reaction of homopropargylic amines with simple imines is developed in the presence of Cu­(OTf)2 and affords a series of hexahydro-1H-pyrrolo­[3,2-c]­quinoline derivatives in good to high yields. This reaction proceeds through an intramolecular hydroamination cyclization of homopropargylic amine to generate a highly reactive dihydropyrrole intermediate in situ. It subsequently reacts with imine via an intermolecular inverse-electron-demand aza-Diels–Alder reaction and a 1,3-H shift to give the fused pyrroloquinoline structures, forming two new C–C bonds and one C–N bond and one N–H bond.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.6b00804