Chiral Carbenoids for Asymmetric Synthesis

• Applicant: Dr. Florian Keller
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2008 to 2009
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 72681178

• Final Report Year: 2009

Final Report Abstract

We have developed a conceptually new route to ß-amino alcohols, a common motif found across a wide spectrum of molecules in chemistry. This associative route employs terminal N-Boc aziridines which are initiated and trapped with boronic esters to give syn-ß-amino, alcohols with complete diastereoselectivity. The process is easily rendered asymmetric and can be used to create carbon chains with multiple stereogenic centers with control over relative and absolute stereochemistry. The regioselectivity in lithiation of N-Bus aryl aziridines is sensitive to the conditions and base employed and this can be used to create 1,2-amino alcohols bearing quaternary stereogenic centers, thus providing a useful route to this especially challenging motif.

Publications

• Stereocontrolled Synthesis of β-Amino Alcohols from Lithiated Aziridines and Boronic Esters, Angew. Chemie 2009, 121, 1169-1172; Angew. Chemie Int. Ed. 2009, 48, 1149-1152
  F. Schmidt, F. Keller, E. Vedrenne, V. K. Aggarwal