Synthesis and applications of diphosphine ligands derived from the lignan hydroxymatairesinol

Yury Brusentsev; Patrik Christoffer Eklund

doi:10.1016/j.cattod.2014.02.032

Synthesis and applications of diphosphine ligands derived from the lignan hydroxymatairesinol

Yury Brusentsev, Patrik Christoffer Eklund

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Abstract

Highly efficient methods for synthetic modifications of the natural lignan hydroxymatairesinol into chiral diphosphines similar to DIOP were developed. Catalytic activity and induction of enantioselectivity for the prepd. phosphines were evaluated in rhodium catalyzed hydrogenations of different functionalized alkenes. High catalytic activities were obsd. with low catalyst loading at atm. pressure. The phosphines showed moderate to high enantioselectivity depending on the substrate used. Hydrogenation of 1-acetamidostyrene gave 84% ee of the S-enantiomer.

Original language	Undefined/Unknown
Pages (from-to)	260–263
Journal	Catalysis Today
Volume	241 Part B
DOIs	https://doi.org/10.1016/j.cattod.2014.02.032
Publication status	Published - 2015
MoE publication type	A1 Journal article-refereed

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10.1016/j.cattod.2014.02.032

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Cite this

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abstract = "Highly efficient methods for synthetic modifications of the natural lignan hydroxymatairesinol into chiral diphosphines similar to DIOP were developed. Catalytic activity and induction of enantioselectivity for the prepd. phosphines were evaluated in rhodium catalyzed hydrogenations of different functionalized alkenes. High catalytic activities were obsd. with low catalyst loading at atm. pressure. The phosphines showed moderate to high enantioselectivity depending on the substrate used. Hydrogenation of 1-acetamidostyrene gave 84% ee of the S-enantiomer.",

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AB - Highly efficient methods for synthetic modifications of the natural lignan hydroxymatairesinol into chiral diphosphines similar to DIOP were developed. Catalytic activity and induction of enantioselectivity for the prepd. phosphines were evaluated in rhodium catalyzed hydrogenations of different functionalized alkenes. High catalytic activities were obsd. with low catalyst loading at atm. pressure. The phosphines showed moderate to high enantioselectivity depending on the substrate used. Hydrogenation of 1-acetamidostyrene gave 84% ee of the S-enantiomer.

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