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

Wang, Qinggang; Leutzsch, Markus; van Gemmeren, Manuel; List, Benjamin

doi:10.1021/ja408747m

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

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Wang, Qinggang
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Leutzsch, Markus
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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van Gemmeren, Manuel
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58764

List, Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Wang, Q., Leutzsch, M., van Gemmeren, M., & List, B. (2013). Disulfonimide-Catalyzed Asymmetric Synthesis of β³-Amino Esters Directly from N-Boc-Amino Sulfones. Journal of the American Chemical Society, 135(41), 15334-15337. doi:10.1021/ja408747m.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0018-D609-1

Abstract

An asymmetric Mannich reaction of silyl ketene acetals with N-Boc-amino sulfones has been developed. A chiral disulfonimide efficiently catalyzes both the in situ generation of the corresponding N-Boc imines and the asymmetric Mannich reaction with excellent yields and enantioselectivities. Kinetic studies confirm a proposed stepwise mechanism.