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Disulfonimide-Catalyzed Asymmetric Synthesis of β3-Amino Esters Directly from N-Boc-Amino Sulfones

Qinggang Wang, Markus Leutzsch, Manuel van Gemmeren and Benjamin List*

*Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany, Email: listkofo.mpg.de

Q. Wang, M. Leutzsch, M. van Gemmeren, B. List, J. Am. Chem. Soc., 2013, 135, 15334-15335.

DOI: 10.1021/ja408747m (free Supporting Information)


Abstract

A chiral disulfonimide efficiently catalyzes an asymmetric Mannich reaction of silyl ketene acetals with N-Boc-amino sulfones with excellent yields and enantioselectivities. The chiral catalyst also promotes the in situ generation of the N-Boc imine intermediates. Kinetic studies confirm a stepwise mechanism.

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Key Words

Mannich Reaction, Organocatalysis


ID: J48-Y2013