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^*

^*Corresponding author for this work

Synthetic and Biomolecular Organic Chemistry

Research output: Contribution to journal › Review article › peer-review

21 Scopus citations

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.

Original language	English
Pages (from-to)	2331-2338
Number of pages	8
Journal	Advanced Synthesis and Catalysis
Volume	354
Issue number	11-12
DOIs	https://doi.org/10.1002/adsc.201200219
State	Published - 2012/08/13

Keywords

asymmetric catalysis
heterogeneous catalysis
immobilization
nitrenes
rhodium

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/adsc.201200219

Cite this

@article{c5e76469f65f4b808c3fa8524f6dc47c,

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",

publisher = "Wiley-VCH Verlag",

number = "11-12",

}

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Fingerprint

Cite this