A Bis-Steroidal Phosphine as New Chiral Hydrogenation Ligand

Enev, Valentin S.; Ewers, Ch. L. J.; Harré, Michael; Nickisch, Klaus; Mohr, Justin T.

doi:10.1021/jo971444p

Cited by 52 publications

(20 citation statements)

References 13 publications

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“…[15] Conclusions Bis(N-arylamino)phosphine-oxazolines have proved to be efficient ligands for the iridium-catalyzed asymmetric hydrogenation of unfunctionalized olefins and, particularly, a,b-unsaturated carboxylic esters. Our results show that these ligands form more reactive iridium catalysts than the previously reported N-sulfonyl derivatives.…”

Section: Iridium-catalyzed Hydrogenationmentioning

confidence: 99%

Chiral Bis(N‐arylamino)phosphine‐oxazolines: Synthesis and Application in Asymmetric Catalysis

Schönleber¹,

Hilgraf²,

Pfaltz³

2008

Adv Synth Catal

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N-Arylation or N-alkylation of chiral 1,2-diamines followed by ring closure with phosphorus trichloride (PCl 3 ) and subsequent coupling with an oxazoline alcohol resulted in a new class of N,P ligands. The corresponding iridium tetrakisA C H T U N G T R E N N U N G [3,5-bis(trifluormethyl)phenyl]borate (BAr F ) complexes were found to be efficient catalysts for the enantioselective hydrogenation of unfunctionalized olefins and a,b-unsaturated carboxylic esters.

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Section: Iridium-catalyzed Hydrogenationmentioning

confidence: 99%

Chiral Bis(N‐arylamino)phosphine‐oxazolines: Synthesis and Application in Asymmetric Catalysis

Schönleber¹,

Hilgraf²,

Pfaltz³

2008

Adv Synth Catal

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“…of (S)-DM-DABN, a chiral aromatic diamine, as a poisoning compound [16]. Here, the R alcohol is obtained in 99.3% ee due to the selective [17], MeO-BI-PHEP [18], C4TunaPhos [19], BIFAP [20], BisbenzodioxanPhos [21], P-phos [22], tetraMe-BITIANP [23], bis-steroidal phosphine [24], and 2A [25]. The reaction can be run in aqueous phase by use of a BINAP derivative with ammonium functions 1Ba [11 b, 26, 27].…”

Section: B-keto Estersmentioning

confidence: 99%

Enantioselective Ketone and β‐Keto Ester Hydrogenations (Including Mechanisms)

Ohkuma¹,

Noyori²

2006

The Handbook of Homogeneous Hydrogenation

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Enantioselective hydrogenation of b-keto esters is a well-established procedure to produce chiral b-hydroxy esters in high optical purity [1][2][3][4]. Many important biologically active compounds have been synthesized through this procedure, even on a commercial scale [1][2][3][4]. Ru complexes [5] bearing appropriate chiral phosphine ligands [6][7][8] provide excellent catalytic efficiency for this reaction. Certain chiral Rh catalysts [3,4] and heterogeneous Ni catalysts [9] are also utilized. The recent development of the chiral diphosphine/diamine-Ru catalyst enables rapid and stereoselective hydrogenation of simple ketones without a hetero-atom functionality close to the carbonyl group [2,4]. These enantioselective transformations are summarized in the present chapter. Chiral LigandsIn enantioselective hydrogenation of ketonic substrates, the excellent catalytic performance such as high turnover number (TON), turnover frequency (TOF = -TON h -1 or s -1 ), and enantioselectivity is achievable only when (pre)catalysts are prepared by the appropriate combination of metal species and chiral ligands [6-8, 10, 11]. Stereo-repulsive interaction between substituents of ligands and substrates is normally utilized for the regulation of stereochemistry. The metal and ligand must be carefully selected because of the diversity of substrate structures [1][2][3][4][5]. Chiral diphosphine ligands with a C 2 symmetry (see Fig. 32.1) have played a main role in this respect. Recently, however, various effective C 1 phosphine ligands as well as phosphinite ligands have been developed, the structures of which are illustrated in Figures 32.2 and 32.3, respectively. Chiral amine and imine ligands (Fig. 32.4) are also useful, particularly when they are coupled with a chiral diphosphine ligand in the hydrogenation of simple ketones [2,4,5]. Immobilized BINAPs are detailed in Figure 32.5.

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“…位, 以及 4,4'位和 7,7'位取代的 BINOL (Scheme 4, 化合物 25～29) [36,37,38] 主要是通过两分子取代萘酚通过偶联反应得到消旋的 BINOL 衍生物, 然后再通过手性试剂参与的拆分过程得到, 此方法步骤较多, 合成比较繁琐. …”

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1,1’-Binaphthalene-2-α-arylmethanol-2’-ols (Ar-BINMOLs) with Axial and sp³-Central Chirality：A Novel Chiral Ligands for Catalytic Asymmetric Transformations

郑龙生¹,

宋涛²,

徐利文³

2014

Chin. J. Org. Chem.

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1-(2-Hydroxynathalen-1-yl)naphthalene-2-ol (BINOL) and its derivatives have been used widely as chiral ligands in asymmetric catalysis. Recently, we have found that the simple axial chiral monoalkylated BINOLs could be converted into synthetically useful and enantiomerically pure 1,1'-binaphthalene-2-α-arylmethanol-2'-ols (Ar-BINMOLs) with axial and sp 3 -central chirality through the axial-to-central chirality transfer of [1,2]-Wittig rearrangement. At present, the catalytic application of Ar-BINMOLs in asymmetric catalysis has been revealed by our and Yus's groups. In this account, the progress in the field of BINOL and its derivatives will also be reported concisely in the article, and the Ar-BINMOLs and its derivatives as new chiral ligands for application in asymmetric catalysis would be summarized detailedly.

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A Bis-Steroidal Phosphine as New Chiral Hydrogenation Ligand

Cited by 52 publications

References 13 publications

Chiral Bis(N‐arylamino)phosphine‐oxazolines: Synthesis and Application in Asymmetric Catalysis

Chiral Bis(N‐arylamino)phosphine‐oxazolines: Synthesis and Application in Asymmetric Catalysis

Enantioselective Ketone and β‐Keto Ester Hydrogenations (Including Mechanisms)

1,1’-Binaphthalene-2-α-arylmethanol-2’-ols (Ar-BINMOLs) with Axial and sp³-Central Chirality：A Novel Chiral Ligands for Catalytic Asymmetric Transformations

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A Bis-Steroidal Phosphine as New Chiral Hydrogenation Ligand

Cited by 52 publications

References 13 publications

Chiral Bis(N‐arylamino)phosphine‐oxazolines: Synthesis and Application in Asymmetric Catalysis

Chiral Bis(N‐arylamino)phosphine‐oxazolines: Synthesis and Application in Asymmetric Catalysis

Enantioselective Ketone and β‐Keto Ester Hydrogenations (Including Mechanisms)

1,1’-Binaphthalene-2-α-arylmethanol-2’-ols (Ar-BINMOLs) with Axial and sp3-Central Chirality：A Novel Chiral Ligands for Catalytic Asymmetric Transformations

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1,1’-Binaphthalene-2-α-arylmethanol-2’-ols (Ar-BINMOLs) with Axial and sp³-Central Chirality：A Novel Chiral Ligands for Catalytic Asymmetric Transformations