Enantioselective Synthesis of 4‑Allyl Tetrahydroquinolines via Copper(I) Hydride-Catalyzed Hydroallylation of 1,2-Dihydroquinolines

CuCl/(R,R)-Ph-BPE-catalyzed asymmetric hydroallylation of 1,2-dihydroquinolines, prepared from readily available quinolines, was developed. The optically active tetrahydroquinolines (THQs) bearing an allylic functionality at position 4 were obtained in good yields and excellent enantioselectivity. T...

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Published inOrganic letters Vol. 22; no. 4; pp. 1530 - 1534
Main Authors Xu-Xu, Qing-Feng, Zhang, Xiao, You, Shu-Li
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.02.2020
Amer Chemical Soc
Subjects
catalytic activity
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
copper
enantioselective synthesis
enantioselectivity
Physical Sciences
quinolines
Science & Technology
ALKENES
KINETIC RESOLUTION
FUNCTIONALIZED TETRAHYDROQUINOLINES
ACID CATALYSIS
ALLYLATION
ALPHA
ASYMMETRIC HYDROGENATION
STEREOSELECTIVE ADDITION
REGIOSELECTIVITY
CROSS METATHESIS
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Summary:CuCl/(R,R)-Ph-BPE-catalyzed asymmetric hydroallylation of 1,2-dihydroquinolines, prepared from readily available quinolines, was developed. The optically active tetrahydroquinolines (THQs) bearing an allylic functionality at position 4 were obtained in good yields and excellent enantioselectivity. The introduced allylic groups are amenable to diverse transformations, thus offering chances to rapidly expand the THQ libraries.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.0c00113