Organocatalytic Allylic Amination of Morita–Baylis–Hillman Carbonates­

Bedřich Formánek; Michal Šimek; Martin Kamlar; Ivana Císařová; Jan Veselý

doi:10.1055/s-0037-1611229

Synthesis, Table of Contents

Synthesis 2019; 51(04): 907-920
DOI: 10.1055/s-0037-1611229

paper

Organocatalytic Allylic Amination of Morita–Baylis–Hillman Carbonates

Bedřich Formánek

^aDepartment of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, 128 43, Prague 2, Czech Republic Email: jxvesely@natur.cuni.czw

,

Michal Šimek

^aDepartment of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, 128 43, Prague 2, Czech Republic Email: jxvesely@natur.cuni.czw

,

Martin Kamlar

^aDepartment of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, 128 43, Prague 2, Czech Republic Email: jxvesely@natur.cuni.czw

,

Ivana Císařová

^bDepartment of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, 128 43, Prague 2, Czech Republic

,

Jan Veselý *

^aDepartment of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, 128 43, Prague 2, Czech Republic Email: jxvesely@natur.cuni.czw

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Abstract

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Dedicated to Prof. Bäckvall to his 70th anniversary.

Abstract

An organocatalytic asymmetric allylic amination of Morita–Baylis–Hillman carbonates with aromatic amines in the presence of β-isocupreidine is described. Chiral allylic amines were obtained in almost quantitative yields (90–96%) with moderate enantioselectivity. Recrystallization afforded products in good yields (45–73%) and high optical purity (82–99% ee). This method provides a facile and efficient route to obtain optically active β-lactams, including the building block of the cholesterol-lowering drug Ezetimibe.

Key words

alkaloids - allylic amination - asymmetric synthesis - Ezetimibe - Morita–Baylis–Hillman carbonates - organocatalysis

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References

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Supplementary Material

Supporting Information

Organocatalytic Allylic Amination of Morita–Baylis–Hillman Carbonates­

Organocatalytic Allylic Amination of Morita–Baylis–Hillman Carbonates