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The Catalytic Asymmetric Abramov Reaction

MPS-Authors
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Guin,  Joyram
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Wang,  Qinggang
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

Guin, J., Wang, Q., van Gemmeren, M., & List, B. (2015). The Catalytic Asymmetric Abramov Reaction. Angewandte Chemie International Edition, 54(1), 355-358. doi:10.1002/anie.201409411.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0024-76B0-8
Abstract
The first catalytic enantioselective Abramov reaction is described. The process is based on the utilization of a chiral disulfonimide catalyst, which efficiently avoids the difficulties encountered with metal-based catalysts. Several functionalized α-hydroxy phosphonates were synthesized in good yields and with excellent enantiomeric ratios of up to >99:1. The process was shown to be scalable and up to 1 g of starting material could be employed under mild reaction conditions.