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Organocatalytic Preparation of Simple β-Hydroxy and β-Amino Esters: Low Catalyst Loadings and Gram-Scale Synthesis

Hao Jiang, Björn Gschwend, Łukasz Albrecht and Karl Anker Jørgensen*

*Center for Catalysis, Aarhus University, 8000 Aarhus C, Denmark, Email: kajchem.au.dk

H. Jiang, B. Gschwend, Ł. Albrecht, K. A. Jørgensen, Org. Lett., 2010, 12, 5052-5055.

DOI: 10.1021/ol102164y (free Supporting Information)


Abstract

A combined amino- and N-heterocyclic carbene (NHC)-catalyzed one-pot reaction sequence using commercially available catalysts at low catalyst loadings gives β-hydroxy and β-amino esters in high yield and excellent enantiopurity. The generation of quaternary stereocenters and application in gram-scale synthesis were also realized, with no requirements of inert or anhydrous reaction conditions.

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Key Words

hydroxylation, amination, sulfonamides, hydrogen peroxide, organocatalysis


ID: J54-Y2010-3200