Cp*Co(III)-Catalyzed gamma-Selective C-H Allylation/Hydroamination Cascade for the Synthesis of Dihydroisoquinolines

  • Choi, Suh Young
  • Kim, Hyeon Dae
  • Park, Jong-Un
  • Park, Sun-a
  • Kim, Ju Hyun
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초록

A Cp*Co(III)-catalyzed gamma-selective C-H allylation/hydroamination cascade toward the synthesis of 3,4-dihydroiSoquinolines (DHIQs) has been successfully developed, starting from NH ketimines and allyl carbonates. Notably, highly efficient and gamma-selective C-H allylations were accomplished using gamma-substituted allyl reagents, thus overcoming the issues of poor alpha/gamma selectivity and low reactivity of previous transition metal-catalyzed C-H allylations. The stereochemistry of allyl carbonates was a crucial factor, and synthesis of the DHIQs was achieved using (Z)-allyl carbonates.

키워드

CATALYZED HYDROAMINATIONOXIDATIVE CYCLIZATIONBISCHLER-NAPIERALSKIALLYLATIONISOQUINOLINEACTIVATIONANNULATIONINHIBITORSINSERTIONALCOHOLS
제목
Cp*Co(III)-Catalyzed gamma-Selective C-H Allylation/Hydroamination Cascade for the Synthesis of Dihydroisoquinolines
저자
Choi, Suh YoungKim, Hyeon DaePark, Jong-UnPark, Sun-aKim, Ju Hyun
DOI
10.1021/acs.orglett.9b03977
발행일
2019-12-20
유형
Article
저널명
Organic Letters
21
24
페이지
10038 ~ 10042