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Nickel-Catalyzed Regio-and Enantioselective Hydroamination of Unactivated Alkenes Using Carbonyl Directing Groups

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Title
Nickel-Catalyzed Regio-and Enantioselective Hydroamination of Unactivated Alkenes Using Carbonyl Directing Groups
Author(s)
Changseok Lee; Hyung-Joon Kang; Huiyeong Seo; Sungwoo Hong
Publication Date
2022-05
Journal
Journal of the American Chemical Society, v.144, no.20, pp.9091 - 9100
Publisher
American Chemical Society
Abstract
© 2022 American Chemical Society.The asymmetric addition of an N-H bond to various alkenes via a direct catalytic method is a powerful way of synthesizing value-added chiral amines. Therefore, the enantio-and regioselective hydroamination of unactivated alkenes remains an appealing goal. Here, we report the highly enantio-and regioselective Ni-catalyzed hydroamination of readily available unactivated alkenes bearing weakly coordinating native amides or esters. This method succeeds for both terminal and internal unactivated alkenes and has a broad amine coupling partner scope. The mild reaction process is well suited for the late-stage functionalization of complex molecules and has the potential to gain modular access to enantioenriched β-or γ-amino acid derivatives and 1,2-or 1,3-diamines. Mechanistic studies reveal that a chiral bisoxazoline-bound Ni specie effectively leverages carbonyl coordination to achieve enantio-and regioselective NiH insertion into alkenes.
URI
https://pr.ibs.re.kr/handle/8788114/11936
DOI
10.1021/jacs.2c02343
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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