A Novel Easily Accessible Chiral Ferrocenyldiphosphine for Highly Enantioselective Hydrogenation, Allylic Alkylation, and Hydroboration Reactions

Togni, Antonio; Breutel, Claude; Schnyder, Anita; Spindler, Felix; Landert, Heidi; Tijani, Amina

doi:10.1021/ja00088a047

Cited by 663 publications

(383 citation statements)

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“…19 It has been widely studied and has found early application in asymmetric Grignard cross-couplings with vinylic halides, mediated by nickel. 19b It also served as the direct precursor to the Josiphos ligands 20 with which we have found some success in early asymmetric versions of this nickel chemistry. 2b…”

Section: Resultsmentioning

confidence: 99%

In situ enzymatic screening (ISES) of P,N-ligands for Ni(0)-mediated asymmetric intramolecular allylic amination

Berkowitz

Shen

Maiti

2004

Tetrahedron: Asymmetry

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Section: Resultsmentioning

confidence: 99%

In situ enzymatic screening (ISES) of P,N-ligands for Ni(0)-mediated asymmetric intramolecular allylic amination

Berkowitz

Shen

Maiti

2004

Tetrahedron: Asymmetry

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“…The method of Solvias starts from the ketone oximes 105, which are readily converted into diphenylphosphorylketimines 107 by treatment with chlorodiphenylphosphane (106; Scheme 45). [109] The asymmetric catalytic hydrogenation in the presence of a Rh I / josiphos(108) catalyst system [110] results in the formation of optically active phosphonamides 109, from which the corresponding chiral amines (R)-110 are released readily by hydrolysis under acidic conditions. Under optimal conditions just 0.2 mol % of the Rh I / 108 catalyst is sufficient for formation of the product 109 with > 99 % ee at complete conversion of 107.…”

Section: Reduction Of C = N Bondsmentioning

confidence: 99%

Industrial Methods for the Production of Optically Active Intermediates

Breuer¹,

Ditrich²,

Habicher³

et al. 2004

Angew Chem Int Ed

1,318

625

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Enantiomerically pure amino acids, amino alcohols, amines, alcohols, and epoxides play an increasingly important role as intermediates in the pharmaceutical industry and agrochemistry, where both a high degree of purity and large quantities of the compounds are required. The chemical industry has primarily relied upon established chemical methods for the synthesis of these intermediates, but is now turning more and more to enzymatic and biotechnological fermentation processes. For the industrial implementation of many transformations alternative methods are available. The advantages of the individual methods will be discussed herein and exemplified by syntheses of relevant compounds.

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“…80 The small angle, 65 , between the two aryl planes (dihedral angle) of the SEGPHOS-Ru complex may cause the high stereoselectivity. BPPM 81 and JOSIPHOS 82 are original for the design of C 1 -chiral diphosphines, whereas the origin of their efficiency is hard to rationalize. Rh complexes with oxoProNOP ligands achieve high catalytic activity and enantioselectivity in hydrogenation of a-keto esters.…”

Section: Hydrogenation Of Simple Olefins With Iridium Catalystsmentioning

confidence: 99%