An Amine Group Transfer Reaction Driven by Aromaticity

A stereoselective domino inverse electron-demand Diels–Alder/amine group transfer reaction catalyzed by a bidentate Lewis acid provides 1-amino-1,2-dihydronaphthalenes, a core structure in many bioactive compounds. A concerted mechanism is proposed based on experimental studies as well as DFT comput...

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Bibliographic Details
Published inOrganic letters Vol. 20; no. 22; pp. 7034 - 7038
Main Authors Ahles, Sebastian, Götz, Silas, Schweighauser, Luca, Brodsky, Mirko, Kessler, Simon N, Heindl, Andreas H, Wegner, Hermann A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.11.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CYCLOADDITION
DOMINO REACTIONS
ONE-POT SYNTHESIS
BIDENTATE
DIELS-ALDER REACTION
ENAMINES
1,2,3-TRIAZINES
ASYMMETRIC TOTAL-SYNTHESIS
SELECTIVE FUNCTIONALIZATION
1-AMINOTETRALINS
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Summary:A stereoselective domino inverse electron-demand Diels–Alder/amine group transfer reaction catalyzed by a bidentate Lewis acid provides 1-amino-1,2-dihydronaphthalenes, a core structure in many bioactive compounds. A concerted mechanism is proposed based on experimental studies as well as DFT computations demonstrating a new general reactivity scheme. The broad scope of the reaction was evaluated by variation of all three starting compounds, phthalazines, aldehydes, and amines. Scalability was demonstrated by a gram scale reaction without diminished yield.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02967