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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;

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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: http://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.