Copper-catalyzed cascade reaction of tryptamines with diazo compounds to access hexahydropyrroloindoline derivatives

A domino reaction sequence of cyclopropanation/ring-opening/iminium cyclization of tryptamine derivatives with donor-acceptor diazo compounds is developed to furnish pyrroloindolines, creating three consecutive stereogenic centers in a single step. The copper-catalyzed reaction provides pyrroloindol...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2022-11, Vol.2 (44), p.861-8614
Main Authors: Kumar, Dharmendra, Chaudhary, Dhananjay, Ishu, Km, Yadav, Suman, Maurya, Naveen Kumar, Kant, Ruchir, Kuram, Malleswara Rao
Format: Article
Language:English
Subjects:
Cascade chemical reactions
Copper
Ring opening
Room temperature
Substrates
Tryptamine
Tryptamines
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Summary:A domino reaction sequence of cyclopropanation/ring-opening/iminium cyclization of tryptamine derivatives with donor-acceptor diazo compounds is developed to furnish pyrroloindolines, creating three consecutive stereogenic centers in a single step. The copper-catalyzed reaction provides pyrroloindolines at room-temperature with good substrate scope. A Cu-catalyzed cyclopropanation/ring-opening/iminium cyclization of tryptamine derivatives with donor-acceptor diazo compounds is developed to furnish pyrroloindolines, creating three consecutive stereogenic centers.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob01635d