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Organocatalytic Asymmetric Mannich Reactions in the Preparation of Enantioenriched β3-Amino Acid Derivatives

[ Vol. 15 , Issue. 13 ]

Author(s):

Luca Bernardi, Alfredo Ricci and Mauro Comes Franchini   Pages 2210 - 2226 ( 17 )

Abstract:


Organocatalytic, asymmetric Mannich reactions giving β3-amino acid derivatives have been reviewed. The Mannich-type addition of an acetate anion to an imine represents in fact one of the most direct routes to this particular class of β-amino acids. However, due to the low acidity of simple acetates, synthetic equivalents of acetate anions had to be used. These include preformed enolates (silylketeneacetals), carbonylic compounds with improved reactivity (acetophenones and their enamines/enamides), acetates equipped with a removable group enhancing their acidity (malonates, nitroacetates, sulfonylacetates, diazoacetates), acetates able to undergo decarboxylative enolate formation (malonic acid half thioesters), and finally acetaldehyde. Each of these equivalents was combined with the requisite organocatalytic strategy, giving very powerful and effective methods for the preparation of β3-amino acid precursors. The simple and straightforward manipulations, used to convert these products into the target β3-amino acid compounds, are also described.

Keywords:

Acetate anion, β-amino acid, asymmetric catalysis, imine, Mannich reaction, organocatalysis, enantioselectivity, (Ee) Enantiomeric excess, (MAHT) Malonic acid half thioester, (Pg) Protecting group, (PTC) Phase-transfer catalysis, (Rfx) Reflux, (Ts) p-toluensulfonyl, MALONIC ACID HALF THIOESTERS 11, Alanine (homoglycine), peptidase enzymes

Affiliation:

Department of Organic Chemistry “A. Mangini”, Faculty of Industrial Chemistry, University of Bologna, V. Risorgimento 4, 40136 Bologna, Italy.



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