Download PDF
Synfacts 2007(1): 0097-0097  
DOI: 10.1055/s-2006-955666
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Synthesis of Isoquinuclidines

Contributor(s): Benjamin List, Sebastian Hoffmann
M. Rueping*, C. Azap
Johann Wolfgang Goethe-Universität, Frankfurt am Main, Germany
Further Information

Publication History

Publication Date:
15 December 2006 (online)

    Permissions and Reprints

Significance

A double Brønsted acid catalyzed enantioselective Mannich-aza-Michael reaction leading to various aromatic and heteroaromatic substituted isoquinuclidines 4 is reported. Brøn­sted acid catalyst 5 activates aldimines 3, whereas acetic acid is proposed to activate enone 1 by shifting the equilibrium towards dienol 2. Furthermore, the authors have shown the importance of choosing a co-catalyst having a certain pKa value to suppress a non-asymmetric reaction pathway. The substituted isoquinuclidines 3 were obtained in moderate to good diastereoselectivities and good enantioselectivities.