Chiral 1,2-Bis(phosphetano)benzenes: Preparation and Use in the Ru-Catalyzed Hydrogenations of Carbonyl Derivatives

Marinetti, Angéla; Genêt, Jean‐Pierre; Jus, Sébastien; Blanc, Delphine; Ratovelomanana‐Vidal, Virginie

doi:10.1002/(sici)1521-3765(19990401)5:4<1160::aid-chem1160>3.0.co;2-3

Cited by 52 publications

(26 citation statements)

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“…Later on this synthetic access has been extended to the synthesis of homologue 1,2-phenylene-bis(phosphetanes) by using other 1,3-diols to give bis(phosphetanes) 4b-d [24] and 4e-g, respectively [25]. The C 2 -symmetrical diphosphines were employed as ligands in the Ru-catalyzed asymmetric hydrogenation of carbonyl compounds.…”

Section: Bidentate Bis(phosphetanes)mentioning

confidence: 99%

Synthesis of Chiral Heterocyclic Phosphines for Application in Asymmetric Catalysis

Holz¹,

Gensow²,

Zayas

et al. 2007

COC

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Section: Bidentate Bis(phosphetanes)mentioning

confidence: 99%

Synthesis of Chiral Heterocyclic Phosphines for Application in Asymmetric Catalysis

Holz¹,

Gensow²,

Zayas

et al. 2007

COC

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“…[47][48][49] With ligands 16, the catalytic activity is moderate, so rather severe reaction conditions must be employed (80 bar, 80°C).…”

Section: Bidentate C 2 -Symmetric Phosphetanesmentioning

confidence: 99%

Synthesis and Properties of Phosphetanes

Marinetti

Carmichael

2002

Chem. Rev.

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“…The rhodium complexes of the ferrocene derivatives 39 have shown useful characteristics for the reduction of itaconates as well as dehydroamino acid derivatives [15,[167][168][169][170]. These compounds are hybrids between ferrocene-based ligands and the various other types.…”

Section: Ferrocene Hybridsmentioning

confidence: 99%

“…These ligands retain the high selectivity of DuPhos. The exception for rhodium-catalyzed reductions are CnrPhos and BPE-4 [168,[264][265][266][267][268]. MalPhos has proven useful for the reductions of b-acylaminoacrylates [260].…”

Section: Duphosmentioning

confidence: 99%

Enantioselective Alkene Hydrogenation: Introduction and Historic Overview

Ager¹

2006

The Handbook of Homogeneous Hydrogenation

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23Enantioselective Alkene Hydrogenation: Introduction and Historic Overview Development of CAMP and DIPAMPDuring the late 1960s, Horner et al. [13] and Knowles and Sabacky [14] independently found that a chiral monodentate tertiary phosphine, in the presence of a rhodium complex, could provide enantioselective induction for a hydrogenation, although the amount of induction was small [15][16][17][18][19][20]. The chiral phosphine ligand replaced the triphenylphosphine in a Wilkinson-type catalyst [10,21,22]. At about this time, it was also found that [Rh(COD) 2 ] + or [Rh(NBD) 2 ] + could be used as catalyst precursors, without the need to perform ligand exchange reactions [23].Knowles found that the monophosphine CAMP (1a) could provide an ee-value of up to 88% for the reduction of dehydroamino acids. CAMP was an extension of PAMP (1b) that provides ee-values of 50-60% in analogous reactions [24]. At this time, Kagan showed that DIOP (2) (vide infra), where the stereogenic centers are not at phosphorus, could also provide enantioselective induction in an hydrogenation. DIOP also showed that a bisphosphine need not have the chirality at phosphorus, and that good stereoselectivity might result from a C 2 -symmetric ligand. Knowles then developed the C 2 -symmetric ligand DIPAMP (3) [22,25]. The use of Rh-DIPAMP for the synthesis of l-Dopa is well known and is still practiced today [12,22,27]. A number of variations of the DIPAMP structure were investigated for the synthesis of this important pharmaceutical, but the parent remains the best ligand in this class [22].

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Chiral 1,2-Bis(phosphetano)benzenes: Preparation and Use in the Ru-Catalyzed Hydrogenations of Carbonyl Derivatives

Cited by 52 publications

References 0 publications

Synthesis of Chiral Heterocyclic Phosphines for Application in Asymmetric Catalysis

Synthesis of Chiral Heterocyclic Phosphines for Application in Asymmetric Catalysis

Synthesis and Properties of Phosphetanes

Enantioselective Alkene Hydrogenation: Introduction and Historic Overview

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