Enantioselective Synthesis of 4‑Aminotetrahydroquinolines via 1,2-Reductive Dearomatization of Quinolines and Copper(I) Hydride-Catalyzed Asymmetric Hydroamination

A 1,2-reductive dearomatization of quinolines and copper­(II) acetate monohydrate/(R,R)-Ph-BPE/P­(p-tolyl)3-catalyzed enantioselective hydroamination sequence was developed, affording diverse 4-amino-1,2,3,4-tetrahydroquinolines with high levels of enantioselectivity in either a stepwise or one-pot...

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Bibliographic Details
Published inOrganic letters Vol. 21; no. 13; pp. 5357 - 5362
Main Authors Xu-Xu, Qing-Feng, Zhang, Xiao, You, Shu-Li
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.07.2019
Amer Chemical Soc
Subjects
alkenes
catalytic activity
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
copper
enantioselective synthesis
enantioselectivity
Physical Sciences
quinolines
Science & Technology
FORMAL HYDROAMINATION
ALKENES
ACID
REAGENTS
AMINES
TETRAHYDROQUINOLINES
TRANSFER HYDROGENATION
STEP
POVAROV REACTION
HYDROXYLAMINE ESTERS
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Summary:A 1,2-reductive dearomatization of quinolines and copper­(II) acetate monohydrate/(R,R)-Ph-BPE/P­(p-tolyl)3-catalyzed enantioselective hydroamination sequence was developed, affording diverse 4-amino-1,2,3,4-tetrahydroquinolines with high levels of enantioselectivity in either a stepwise or one-pot fashion. Pleasingly, internal cis-cyclic alkenes, which are challenging substrates in copper hydride-catalyzed enantioselective hydroamination reactions, were transformed efficiently under mild conditions.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.9b02034