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

• Here, we report the first Ir-N,P complex catalyzed tandem Peterson olefination and asymmetric hydrogenation of -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 -hydroxy silane in a chemoselective manner. Additionally, based on this method, an expedient enantioselective synthesis of (S)-(+)--curcumene, from a simple ketone, was accomplished in two steps with 75% overall yield and 95% ee.

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NATURVETENSKAP  -- Kemi -- Organisk kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences -- Organic Chemistry (hsv//eng)

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