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2009•European Journal of Organic ChemistryOpen access

Enantioselective Ag‐Catalyzed Allylation of Aldimines

Marina Naodovic, Manabu Wadamoto, Hisashi Yamamoto

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Abstract

A highly enantioselective synthesis of homoallylic amines, using allyltrimethoxysilane under Ag(I) catalytic conditions, has been developed. Among the chiral ligands investigated, a remarkable difference in the resulting Ag(I) complexes was observed. Under mild conditions and low catalyst loadings, homoallylamines were produced in high ee values (up to 80%) and good yields. The methodology can be further extended to a diastere- and enantioselective crotylation of aldimines.

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What this paper is about

A highly enantioselective synthesis of homoallylic amines, using allyltrimethoxysilane under Ag(I) catalytic conditions, has been developed. Among the chiral ligands investigated, a remarkable difference in the resulting Ag(I) complexes was observed. Under mild conditions and low catalyst loadings, homoallylamines were produced in high ee values (up to 80%) and good yields. The methodology can be further extended to a diastere- and enantioselective crotylation of aldimines.

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Available abstract

A highly enantioselective synthesis of homoallylic amines, using allyltrimethoxysilane under Ag(I) catalytic conditions, has been developed. Among the chiral ligands investigated, a remarkable difference in the resulting Ag(I) complexes was observed. Under mild conditions and low catalyst loadings, homoallylamines were produced in high ee values (up to 80%) and good yields. The methodology can be further extended to a diastere- and enantioselective crotylation of aldimines.

Key concepts: Enantioselective synthesis, Aldimine, Chemistry, Catalysis, Organic chemistry

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