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Rhodium/Ruthenium Applications

  • Kenzo SumiEmail author
  • Hidenori Kumobayashi
Chapter
Part of the Topics in Organometallic Chemistry book series (TOPORGAN, volume 6)

Abstract

Asymmetric catalytic hydrogenation and hydrogen transfer reactions of various substrates such as prochiral ketones and olefins using Rh(I) and Ru(II) complexes will be reviewed. These asymmetric transformations have provided organic chemists with efficient routes to a wide variety of optically active compounds with important biological activities. Based on the success and the marvelous abilities of the BINAP ligand, new analogues of BINAP and SEGPHOS ligands have been developed. This review surveys recent advances in industrial chiral technology using rhodium and ruthenium catalysts.

Keywords

Rh Ru Ligand Asymmetric Catalytic 

List of Abbreviations and Symbols

ADHD

Attention-deficit hyperactivity disorder

BDPP

2,4-Bis(diphenylphosphino)pentane

BINAP

2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl

(R,S)-BINAPHOS

(R)-2-(Diphenylphosphino)-1,1′-binaphthalen-2′-yl (S)-1,1′-binaphthalene-2,2′-diyl phosphite

BIPHEMP

(6,6′-Dimethylbiphenyl-2,2′-diyl)bis(diphenylphosphine)

BIPNOR

2,2′,3,3′-Tetraphenyl-4,4′,5,5′-tetramethyl-6,6′-bis-1-phosphanorborna-2,5-dienyl

BPPM

N-(tert-Butoxycarbonyl)-4-(diphenylphosphino)-2-[(diphenylphosphino)methyl]pyrrolidine

c

cyclo

DAIPEN

1-Isopropyl-2,2-bis(p-methoxyphenyl)-1,2-ethylenediamine

DBT

Dibenzoyl tartrate

DIOP

2,3-O-Isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane

DIPAMP

1,2-Bis(o-anisylphenylphosphino)ethane

DPEN

1,2-Diphenylethylenediamine

H8-BINAP

2,2′-Bis(diphenylphosphino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl

HMG-CoA

3-Hydroxy-3-methylglutaryl coenzyme-A

(R,R)-Me-DuPHOS

(−)-1,2-Bis[(2R,5R)-2,5-dimethylphospholano]benzene

MeO-BIPHEP

(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis(diphenylphosphine)

2-Nap-BIPNITE-p-F

2-Di(2-naphthyl)phosphino-2′-bis(4-fluorophenyl)phosphinoxy-1,1′-binaphthyl

[2.2]PHANEPHOS

4,12-Bis(diphenylphosphino)-[2.2]-paracyclophane

S/C

Substrate-to-catalyst ratio

SEGPHOS

(4,4′-Bi-1,3-benzodioxole)-5,5′-diylbis(diarylphosphine)

TON

Turnover number

TBDEMS (TBS)

tert-Butyldimethylsilyl

θ

Dihedral angle

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Authors and Affiliations

  1. 1.Central Research LaboratoryTakasago International CorporationHiratsuka-CityJapan

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