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Nickel-Catalyzed Hydrocyanation of Allenes and Its Application

Journal

CHEMICAL & PHARMACEUTICAL BULLETIN
Volume 67, Issue 5, Pages 397-403

Publisher

PHARMACEUTICAL SOC JAPAN
DOI: 10.1248/cpb.c18-00953

Keywords

alkaloid; allene; catalysis; cyanation; cyclization; nickel

Funding

  1. Japan Society for the Promotion of Science (JSPS)
  2. Uehara Memorial Foundation
  3. Naito Foundation

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Cyano (CN) groups are equivalent to carbonyl as well as amino- and hydroxymethyl groups. Therefore, their catalytic introduction under metal catalysis is an important issue in synthetic organic chemistry. Ni-catalyzed hydrocyanation is one of the most well-investigated, powerful tools for installing a CN group. However, it is still difficult to control chemo- and regioselectivity. In this review, the author uses allenes to enable regio-, stereo-, and face-selective transformations to natural product synthesis and axial chirality transfer.

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