Highly Enantio- and Diastereoselective Organocatalytic Asymmetric Domino Michael–Aldol Reaction of β-Ketoesters and α,β-Unsaturated Ketones†
Nis Halland Dr.
The Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark, Fax:(+45) 8919-6199
Search for more papers by this authorPompiliu S. Aburel Dr.
The Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark, Fax:(+45) 8919-6199
Search for more papers by this authorKarl Anker Jørgensen Prof. Dr.
The Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark, Fax:(+45) 8919-6199
Search for more papers by this authorNis Halland Dr.
The Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark, Fax:(+45) 8919-6199
Search for more papers by this authorPompiliu S. Aburel Dr.
The Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark, Fax:(+45) 8919-6199
Search for more papers by this authorKarl Anker Jørgensen Prof. Dr.
The Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark, Fax:(+45) 8919-6199
Search for more papers by this authorWe are grateful to Dr. R. G. Hazell for X-ray crystallographic analysis of compounds 6 a, c, e. This work was made possible by a grant from The Danish National Research Foundation.
Graphical Abstract
Three to four contiguous stereogenic centers are formed in the title reaction (see scheme). The optically active cyclohexanones are formed as single diastereomers with excellent enantioselectivities (up to 99 % ee) and can be transformed into synthetically useful building blocks.
Supporting Information
Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2004/z53364_s.pdf or from the author.
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
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- 14The reaction rate is strongly concentration-dependent (see Supporting Information).
