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Tandem Peterson olefination and chemoselective asymmetric hydrogenation of ?-hydroxy silanes.

ABSTRACT: 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.

SUBMITTER: Krajangsri S

PROVIDER: S-EPMC6438149 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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

Krajangsri Suppachai S Wu Haibo H Liu Jianguo J Rabten Wangchuk W Singh Thishana T Andersson Pher G PG

Chemical science 20190204 12

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 ...[more]

PMID: 30996960

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