Synthesis 2019; 51(04): 907-920
DOI: 10.1055/s-0037-1611229
paper
© Georg Thieme Verlag Stuttgart · New York

Organocatalytic Allylic Amination of Morita–Baylis–Hillman Carbonates­

Bedřich Formánek
a  Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, 128 43, Prague 2, Czech Republic   Email: jxvesely@natur.cuni.czw
,
Michal Šimek
a  Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, 128 43, Prague 2, Czech Republic   Email: jxvesely@natur.cuni.czw
,
Martin Kamlar
a  Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, 128 43, Prague 2, Czech Republic   Email: jxvesely@natur.cuni.czw
,
Ivana Císařová
b  Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, 128 43, Prague 2, Czech Republic
,
a  Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, 128 43, Prague 2, Czech Republic   Email: jxvesely@natur.cuni.czw
› Author Affiliations
Jan Veselý gratefully acknowledges the Czech Science Foundation (No 16-23597S) for financial support. Bedřich Formánek thanks the Charles University Grant Agency (grant number 392315) for financial support.
Further Information

Publication History

Received: 28:08:2018

Accepted after revision: 01:10:2018

Publication Date:
25 October 2018 (eFirst)

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.

Supporting Information

 
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