Catalytic enantioselective Hosomi-Sakurai reaction of α-ketoesters promoted by chiral copper(ii) complexes

Yutaro Niwa; Mayu Miyake; Ichiro Hayakawa; Akira Sakakura

doi:10.1039/c9cc01159e

Catalytic enantioselective Hosomi-Sakurai reaction of α-ketoesters promoted by chiral copper(ii) complexes

Yutaro Niwa, Mayu Miyake, Ichiro Hayakawa, Akira Sakakura

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

2 Citations (Scopus)

Abstract

A catalytic enantioselective Hosomi-Sakurai reaction of α-ketoesters has been developed. A copper(ii) complex with a chiral bis(oxazoline) ligand bearing methanesulfonamide groups shows excellent catalytic activity to give α,α-disubstituted α-hydroxyesters in high yields with high enantioselectivities. This is the first successful method for the catalytic enantioselective 1,2-addition of α-ketoesters with allylic silanes.

Original language	English
Pages (from-to)	3923-3926
Number of pages	4
Journal	Chemical Communications
Volume	55
Issue number	27
DOIs	https://doi.org/10.1039/c9cc01159e
Publication status	Published - 2019

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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title = "Catalytic enantioselective Hosomi-Sakurai reaction of α-ketoesters promoted by chiral copper(ii) complexes",

abstract = "A catalytic enantioselective Hosomi-Sakurai reaction of α-ketoesters has been developed. A copper(ii) complex with a chiral bis(oxazoline) ligand bearing methanesulfonamide groups shows excellent catalytic activity to give α,α-disubstituted α-hydroxyesters in high yields with high enantioselectivities. This is the first successful method for the catalytic enantioselective 1,2-addition of α-ketoesters with allylic silanes.",

author = "Yutaro Niwa and Mayu Miyake and Ichiro Hayakawa and Akira Sakakura",

note = "Funding Information: Financial support for this project was partially provided by a Grant-in-Aid from JSPS KAKENHI (18K05123), the Sumitomo Foundation and the Okayama Foundation for Science and Technology. The authors gratefully thank the Division of Instrumental Analysis, Department of Instrumental Analysis & Cryogenics, Advanced Science Research Center, Okayama University for the NMR and HRMS measurements.",

year = "2019",

doi = "10.1039/c9cc01159e",

language = "English",

volume = "55",

pages = "3923--3926",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "27",

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T1 - Catalytic enantioselective Hosomi-Sakurai reaction of α-ketoesters promoted by chiral copper(ii) complexes

AU - Niwa, Yutaro

AU - Miyake, Mayu

AU - Hayakawa, Ichiro

AU - Sakakura, Akira

N1 - Funding Information: Financial support for this project was partially provided by a Grant-in-Aid from JSPS KAKENHI (18K05123), the Sumitomo Foundation and the Okayama Foundation for Science and Technology. The authors gratefully thank the Division of Instrumental Analysis, Department of Instrumental Analysis & Cryogenics, Advanced Science Research Center, Okayama University for the NMR and HRMS measurements.

PY - 2019

Y1 - 2019

N2 - A catalytic enantioselective Hosomi-Sakurai reaction of α-ketoesters has been developed. A copper(ii) complex with a chiral bis(oxazoline) ligand bearing methanesulfonamide groups shows excellent catalytic activity to give α,α-disubstituted α-hydroxyesters in high yields with high enantioselectivities. This is the first successful method for the catalytic enantioselective 1,2-addition of α-ketoesters with allylic silanes.

AB - A catalytic enantioselective Hosomi-Sakurai reaction of α-ketoesters has been developed. A copper(ii) complex with a chiral bis(oxazoline) ligand bearing methanesulfonamide groups shows excellent catalytic activity to give α,α-disubstituted α-hydroxyesters in high yields with high enantioselectivities. This is the first successful method for the catalytic enantioselective 1,2-addition of α-ketoesters with allylic silanes.

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