Binaphthol-derived phosphoric acids as efficient chiral organocatalysts for the enantiomer-selective polymerization of rac-lactide

Kosuke Makiguchi; Takuto Yamanaka; Toyoji Kakuchi; Masahiro Terada; Toshifumi Satoh

doi:10.1039/c4cc00215f

Binaphthol-derived phosphoric acids as efficient chiral organocatalysts for the enantiomer-selective polymerization of rac-lactide

Kosuke Makiguchi, Takuto Yamanaka, Toyoji Kakuchi, Masahiro Terada, Toshifumi Satoh

SCI - Chemistry

Research output: Contribution to journal › Article › peer-review

53 Citations (Scopus)

Abstract

A high enantiomer-selectivity for the polymerization of rac-lactide was achieved using chiral binaphthol-derived monophosphoric acids as organocatalysts. During the polymerization, d-lactide (DLA) preferentially polymerized via kinetic resolution with the maximum selectivity factor (k _D/k_L) of 28.3. The selective polymerization of DLA was derived from a dual activation, i.e., monomer activation and chain-end activation.

Original language	English
Pages (from-to)	2883-2885
Number of pages	3
Journal	Chemical Communications
Volume	50
Issue number	22
DOIs	https://doi.org/10.1039/c4cc00215f
Publication status	Published - 2014 Mar 18

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/c4cc00215f

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AU - Makiguchi, Kosuke

AU - Yamanaka, Takuto

AU - Kakuchi, Toyoji

AU - Terada, Masahiro

AU - Satoh, Toshifumi

PY - 2014/3/18

Y1 - 2014/3/18

N2 - A high enantiomer-selectivity for the polymerization of rac-lactide was achieved using chiral binaphthol-derived monophosphoric acids as organocatalysts. During the polymerization, d-lactide (DLA) preferentially polymerized via kinetic resolution with the maximum selectivity factor (k D/kL) of 28.3. The selective polymerization of DLA was derived from a dual activation, i.e., monomer activation and chain-end activation.

AB - A high enantiomer-selectivity for the polymerization of rac-lactide was achieved using chiral binaphthol-derived monophosphoric acids as organocatalysts. During the polymerization, d-lactide (DLA) preferentially polymerized via kinetic resolution with the maximum selectivity factor (k D/kL) of 28.3. The selective polymerization of DLA was derived from a dual activation, i.e., monomer activation and chain-end activation.

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Binaphthol-derived phosphoric acids as efficient chiral organocatalysts for the enantiomer-selective polymerization of rac-lactide

Abstract

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