Catalytic Asymmetric Strecker Reaction of Ketoimines with Potassium Cyanide

A catalytic asymmetric Strecker reaction of ketoimines with potassium cyanide (KCN) is developed. Control experiments reveal the involvement of a retro‐Strecker reaction, which inevitably decreases the product yield and enantioselectivity. The use of a protic additive in combination with a chiral 1,...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2021-12, Vol.10 (12), p.3237-3240
Main Authors: Ohmatsu, Kohsuke, Morita, Yusuke, Kiyokawa, Mari, Hoshino, Kimihiro, Ooi, Takashi
Format: Article
Language:English
Subjects:
asymmetric synthesis
Asymmetry
cyanide ion
Cyanides
Enantiomers
Organic chemistry
organic molecular catalyst
phase-transfer catalyst
Potassium
Potassium cyanide
triazolium
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Summary:A catalytic asymmetric Strecker reaction of ketoimines with potassium cyanide (KCN) is developed. Control experiments reveal the involvement of a retro‐Strecker reaction, which inevitably decreases the product yield and enantioselectivity. The use of a protic additive in combination with a chiral 1,2,3‐triazolium ion as a catalyst allows for the highly efficient and enantioselective cyanide addition to various ketoimines. The chiral 1,2,3‐triazolium ions featuring preeminent anion‐binding ability enable the efficient solid‐liquid or liquid‐liquid extraction of cyanide ions and ensuring delivery to ketoimines with high levels of enantiocontrol. The present method provides a straightforward access to enantiomerically enriched, synthetically versatile α‐amino nitriles possessing tetrasubstituted chiral carbon.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202100608