Concise Synthesis of α-Trisubstituted Amines from Ketones Using N-Methoxyamines

Three-component allylation and cyanation utilizing a ketone and an N-methoxyamine are reported. The high nucleophilicity of the N-methoxyamine and high electrophilicity of the corresponding iminium ion enable the concise synthesis of α-trisubstituted amines in a single step.

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Bibliographic Details
Published in:Organic letters 2012-04, Vol.14 (8), p.2098-2101
Main Authors: Kurosaki, Yusuke, Shirokane, Kenji, Oishi, Takeshi, Sato, Takaaki, Chida, Noritaka
Format: Article
Language:English
Subjects:
Amines - chemical synthesis
Amines - chemistry
Catalysis
Ketones - chemistry
Molecular Structure
Stereoisomerism
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Description
Summary:Three-component allylation and cyanation utilizing a ketone and an N-methoxyamine are reported. The high nucleophilicity of the N-methoxyamine and high electrophilicity of the corresponding iminium ion enable the concise synthesis of α-trisubstituted amines in a single step.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol300622r