4.7 Review

Direct Asymmetric Addition of Heteroatom Nucleophiles to Imines

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 364, Issue 13, Pages 2092-2112

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202200155

Keywords

Asymmetric addition; Imines; Asymmetric synthesis; Heteroatom nucleophiles; Chiral catalysts; Kabachnik-Fields reactions

Funding

  1. Grants Council of the President of the Russian Federation [N.Sh.1223.2022.1.3]
  2. Russian Science Foundation [21-13-00304]
  3. Russian Science Foundation [21-13-00304] Funding Source: Russian Science Foundation

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This review focuses on the asymmetric addition reactions of non-carbon nucleophiles to imines. Chiral catalysts are used to achieve control over the stereochemistry of the addition reactions.
The direct asymmetric addition of heteroatom nucleophiles to imines represents one of the most efficient tools for the formation of carbon-heteroatom bonds and has received much interest recently. The review is devoted to the asymmetric addition reactions of non-carbon nucleophiles to imines. The present review is divided into five main sections: reactions with N-nucleophiles; reactions with P-nucleophiles; reactions with O-nucleophiles; reactions with S-nucleophiles; reactions with Se-nucleophiles. It has been seen that chiral catalysts such as quinines, BINOLs, chiral phosphoric acids as well as various Bronsted and Lewis acids are the source of asymmetry of the presented reactions of asymmetric addition of non-carbon nucleophiles to imines.

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