Palladium-catalyzed asymmetric [3 + 2] cycloaddition of 5-vinyloxazolidinones with imines using chiral ammonium-phosphine hybrid ligand

Kohsuke Ohmatsu; Shinya Kawai; Naomichi Imagawa; Takashi Ooi

doi:10.1021/cs501369z

Palladium-catalyzed asymmetric [3 + 2] cycloaddition of 5-vinyloxazolidinones with imines using chiral ammonium-phosphine hybrid ligand

Kohsuke Ohmatsu
, Shinya Kawai
, Naomichi Imagawa
, Takashi Ooi

研究成果: Article › 査読

78 被引用数 (Scopus)

抄録

A palladium-catalyzed asymmetric [3 + 2] annulation reaction between racemic 5-vinyloxazolidinones and N-sulfonyl imines was established. Under the influence of the palladium complex with a chiral ammonium-phosphine hybrid ligand, the cycloaddition proceeded smoothly to yield imidazolidines bearing α-amino quaternary stereocenters in high yields with excellent diastereo- and enantioselectivities.

本文言語	English
ページ（範囲）	4304-4306
ページ数	3
ジャーナル	ACS Catalysis
巻	4
号	12
DOI	https://doi.org/10.1021/cs501369z
出版ステータス	Published - 2014 12月 5
外部発表	はい

ASJC Scopus subject areas

触媒
化学一般

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10.1021/cs501369z

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引用スタイル

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abstract = "A palladium-catalyzed asymmetric [3 + 2] annulation reaction between racemic 5-vinyloxazolidinones and N-sulfonyl imines was established. Under the influence of the palladium complex with a chiral ammonium-phosphine hybrid ligand, the cycloaddition proceeded smoothly to yield imidazolidines bearing α-amino quaternary stereocenters in high yields with excellent diastereo- and enantioselectivities.",

keywords = "ammonium ion, asymmetric catalysis, cycloaddition, imidazolidine, palladium, phosphine",

author = "Kohsuke Ohmatsu and Shinya Kawai and Naomichi Imagawa and Takashi Ooi",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

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AU - Imagawa, Naomichi

AU - Ooi, Takashi

PY - 2014/12/5

Y1 - 2014/12/5

N2 - A palladium-catalyzed asymmetric [3 + 2] annulation reaction between racemic 5-vinyloxazolidinones and N-sulfonyl imines was established. Under the influence of the palladium complex with a chiral ammonium-phosphine hybrid ligand, the cycloaddition proceeded smoothly to yield imidazolidines bearing α-amino quaternary stereocenters in high yields with excellent diastereo- and enantioselectivities.

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KW - ammonium ion

KW - asymmetric catalysis

KW - cycloaddition

KW - imidazolidine

KW - palladium

KW - phosphine

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