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Issue 12, 2019
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Tandem Peterson olefination and chemoselective asymmetric hydrogenation of β-hydroxy silanes

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Abstract

Here, we report the first Ir–N,P complex catalyzed tandem Peterson olefination and asymmetric hydrogenation of β-hydroxy silanes. This reaction resulted in the formation of chiral alkanes in high isolated yields (up to 99%) and excellent enantioselectivity (up to 99% ee) under mild conditions. Modification of the reaction conditions provides a choice to transform either an olefin or the β-hydroxy silane in a chemoselective manner. Additionally, based on this method, an expedient enantioselective synthesis of (S)-(+)-α-curcumene, from a simple ketone, was accomplished in two steps with 75% overall yield and 95% ee.

Graphical abstract: Tandem Peterson olefination and chemoselective asymmetric hydrogenation of β-hydroxy silanes

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Publication details

The article was received on 26 Nov 2018, accepted on 03 Feb 2019 and first published on 04 Feb 2019


Article type: Edge Article
DOI: 10.1039/C8SC05261A
Citation: Chem. Sci., 2019,10, 3649-3653
  • Open access: Creative Commons BY-NC license
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    Tandem Peterson olefination and chemoselective asymmetric hydrogenation of β-hydroxy silanes

    S. Krajangsri, H. Wu, J. Liu, W. Rabten, T. Singh and P. G. Andersson, Chem. Sci., 2019, 10, 3649
    DOI: 10.1039/C8SC05261A

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