Enantioselective Synthesis of Quaternary Carbon Stereogenic Centers through the Primary Amine-Catalyzed Michael Addition Reaction of α-Substituted Cyclic Ketones at High Pressure

The enantioselective Michael addition reaction of α‐substituted cyclic ketones with acrylates was efficiently promoted by a primary amine chiral catalyst under high‐pressure conditions (1.0 GPa) in tetrahydrofuran. This method was highly successful for the construction of an all‐carbon‐substituted q...

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Bibliographic Details
Published in:European journal of organic chemistry 2015-07, Vol.2015 (20), p.4457-4463
Main Authors: Horinouchi, Ryo, Kamei, Kouhei, Watanabe, Riki, Hieda, Nobushige, Tatsumi, Naoki, Nakano, Keiji, Ichikawa, Yoshiyasu, Kotsuki, Hiyoshizo
Format: Article
Language:English
Subjects:
Asymmetric catalysis
High-pressure chemistry
Ketones
Michael addition
Organocatalysis
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Summary:The enantioselective Michael addition reaction of α‐substituted cyclic ketones with acrylates was efficiently promoted by a primary amine chiral catalyst under high‐pressure conditions (1.0 GPa) in tetrahydrofuran. This method was highly successful for the construction of an all‐carbon‐substituted quaternary‐carbon stereogenic center at the α‐position of cyclic ketones in high enantiomeric excess, and could be conveniently applied to the formal synthesis of (+)‐aspidospermidine. The Michael addition reaction of α‐substituted cyclic ketones was efficiently promoted by a primary amine‐based organocatalyst under high‐pressure conditions (1.0 GPa) in tetrahydrofuran.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201500411