A polymer-supported chiral fluorinated dirhodium(II) complex for asymmetric amination of silyl enol ethers

Tadashi Oohara; Hisanori Nambu; Masahiro Anada; Koji Takeda; Shunichi Hashimoto

doi:10.1002/adsc.201200219

A polymer-supported chiral fluorinated dirhodium(II) complex for asymmetric amination of silyl enol ethers

Tadashi Oohara, Hisanori Nambu, Masahiro Anada, Koji Takeda, Shunichi Hashimoto^*

^*この論文の責任著者

分子合成化学研究室

研究成果: ジャーナルへの寄稿 › 総説 › 査読

21 被引用数 (Scopus)

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The immobilization of dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)- tert-leucinate], [Rh ₂(S-TFPTTL) ₄], has been accomplished by copolymerization of a dirhodium(II) complex-containing monomer with styrene and 1,6-bis(4-vinylbenzyloxy)hexane as a flexible cross-linker. The polymer-supported chiral fluorinated dirhodium(II) complex catalyzed the amination of silyl enol ethers with [N-(2-nitrophenylsulfonyl)imino] phenyliodinane (NsN=IPh) to provide α-amino ketones in high yields with high levels of enantioselectivity and could be used up to 20 times as the catalyst readily withstood stirring in the presence of the solid reactant.

本文言語	英語
ページ（範囲）	2331-2338
ページ数	8
ジャーナル	Advanced Synthesis and Catalysis
巻	354
号	11-12
DOI	https://doi.org/10.1002/adsc.201200219
出版ステータス	出版済み - 2012/08/13

ASJC Scopus 主題領域

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有機化学

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10.1002/adsc.201200219

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title = "A polymer-supported chiral fluorinated dirhodium(II) complex for asymmetric amination of silyl enol ethers",

abstract = "The immobilization of dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)- tert-leucinate], [Rh 2(S-TFPTTL) 4], has been accomplished by copolymerization of a dirhodium(II) complex-containing monomer with styrene and 1,6-bis(4-vinylbenzyloxy)hexane as a flexible cross-linker. The polymer-supported chiral fluorinated dirhodium(II) complex catalyzed the amination of silyl enol ethers with [N-(2-nitrophenylsulfonyl)imino] phenyliodinane (NsN=IPh) to provide α-amino ketones in high yields with high levels of enantioselectivity and could be used up to 20 times as the catalyst readily withstood stirring in the presence of the solid reactant.",

keywords = "asymmetric catalysis, heterogeneous catalysis, immobilization, nitrenes, rhodium",

author = "Tadashi Oohara and Hisanori Nambu and Masahiro Anada and Koji Takeda and Shunichi Hashimoto",

year = "2012",

month = aug,

day = "13",

doi = "10.1002/adsc.201200219",

language = "英語",

volume = "354",

pages = "2331--2338",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

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TY - JOUR

T1 - A polymer-supported chiral fluorinated dirhodium(II) complex for asymmetric amination of silyl enol ethers

AU - Oohara, Tadashi

AU - Nambu, Hisanori

AU - Anada, Masahiro

AU - Takeda, Koji

AU - Hashimoto, Shunichi

PY - 2012/8/13

Y1 - 2012/8/13

N2 - The immobilization of dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)- tert-leucinate], [Rh 2(S-TFPTTL) 4], has been accomplished by copolymerization of a dirhodium(II) complex-containing monomer with styrene and 1,6-bis(4-vinylbenzyloxy)hexane as a flexible cross-linker. The polymer-supported chiral fluorinated dirhodium(II) complex catalyzed the amination of silyl enol ethers with [N-(2-nitrophenylsulfonyl)imino] phenyliodinane (NsN=IPh) to provide α-amino ketones in high yields with high levels of enantioselectivity and could be used up to 20 times as the catalyst readily withstood stirring in the presence of the solid reactant.

AB - The immobilization of dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)- tert-leucinate], [Rh 2(S-TFPTTL) 4], has been accomplished by copolymerization of a dirhodium(II) complex-containing monomer with styrene and 1,6-bis(4-vinylbenzyloxy)hexane as a flexible cross-linker. The polymer-supported chiral fluorinated dirhodium(II) complex catalyzed the amination of silyl enol ethers with [N-(2-nitrophenylsulfonyl)imino] phenyliodinane (NsN=IPh) to provide α-amino ketones in high yields with high levels of enantioselectivity and could be used up to 20 times as the catalyst readily withstood stirring in the presence of the solid reactant.

KW - asymmetric catalysis

KW - heterogeneous catalysis

KW - immobilization

KW - nitrenes

KW - rhodium

UR - http://www.scopus.com/inward/record.url?scp=84865020079&partnerID=8YFLogxK

U2 - 10.1002/adsc.201200219

DO - 10.1002/adsc.201200219

M3 - 総説

AN - SCOPUS:84865020079

SN - 1615-4150

VL - 354

SP - 2331

EP - 2338

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 11-12

ER -

A polymer-supported chiral fluorinated dirhodium(II) complex for asymmetric amination of silyl enol ethers

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