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Catalytic Asymmetric Formal Insertion of Aryldiazoalkanes into the C-H Bond of Aldehydes: Synthesis of Enantioenriched Acyclic α-Tertiary Aryl Ketones

Byung Chul Kang, Dong Guk Nam, Geum-Sook Hwang* and Do Hyun Ryu*

*Department of Chemistry, Sungkyunkwan University, Suwon, 440-746; Western Seoul Center, Korea Basic Science Institute, Seoul 120-140, Korea, Email: gshwangkbsi.re.kr, dhryuskku.edu

B. C. Kang, D. G. Nam, G.-S. Hwang, D.-H. Ryu, Org. Lett., 2015, 17, 4810-4813.

DOI: 10.1021/acs.orglett.5b02370 (free Supporting Information)



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Abstract

Boron Lewis acid promoted formal insertion of aryldiazoalkane into the C-H bond of both aromatic and aliphatic aldehydes enables a novel, catalytic enantioselective route to α-tertiary aryl ketones. In the presence of a chiral (S)-oxazaborolidinium ion catalyst, the reaction proceeded in good yields with excellent enantioselectivities.

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Key Words

acylation, benzylation


ID: J54-Y2015