Optically active (2-aminomethylferrocenyl) phosphines with the phosphorus chiral center

Troitskaya, L. L.; Starikova, Z. A.; Demeshchik, T. V.; Sokolov, V. I.

doi:10.1007/bf02494822

Cited by 17 publications

(8 citation statements)

References 11 publications

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“…Our group has been interested in reactions of CPCs with alkali metal phosphides because of possible transformations of cyclopalladated complexes into aminophosphines, diphosphines and related compounds containing a PR 2 group and another functionality. Previously, brief studies by Sokolov et al [3,4], Bolm et al [5] and Dunina et al [6] revealed that PPh 3 adducts of C,N-cyclopalladated complexes react with LiPPh 2 or KPPh 2 to yield either the corresponding aminophosphines or their Pd(0) complexes. Recently, we reported a detailed investigation of the LiPPh 2 reactions with the dinuclear chloro-bridged CPC 1 and showed that three products are formed in these transformations: (1) the corresponding mononuclear derivative 2 with Ph 2 P(CH 2 ) 4 OH as an auxiliary ligand, (2) complex 3, which is the m-Cl-m-PPh 2 analog of dimer 1, and (3) ortho-(diphenylphosphino)benzylamine 4 (Scheme 1) [7].…”

Section: Introductionmentioning

confidence: 99%

Chemoselectivity control in the reaction of a dinuclear chloro-bridged cyclopalladated complex with potassium diphenylphosphide

Stepanova

Dunina

Smoliakova

2011

Journal of Organometallic Chemistry

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Section: Introductionmentioning

confidence: 99%

Chemoselectivity control in the reaction of a dinuclear chloro-bridged cyclopalladated complex with potassium diphenylphosphide

Stepanova

Dunina

Smoliakova

2011

Journal of Organometallic Chemistry

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“…Later, the same group published results obtained for the reaction of (S pl ,S pl )-91 with the prochiral lithium phosphide, LiPMePh (Scheme 31) [67]. Two diastereomers of aminophosphine 92 were obtained in 52% total yield and were separated using column chromatography on silica gel.…”

Section: Reactions Of Cyclopalladated Complexes With Metal Phosphidesmentioning

confidence: 99%

Synthesis of Aminophosphines and Their Applications in Catalysis

Stepanova¹,

Smoliakova²

2012

COC

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The review describes preparation of P,N-bidentate ligands without a P-N bond and their use in asymmetric catalysis. Diverse types of aminophosphines are considered with emphasis on P,N-ferrocene ligands, phosphino-oxazolines and phosphinopyridines. The following major synthetic approaches to aminophosphines and related compounds are summarized: (i) via lithiation, (ii) the use of Grignard reagents, (iii) nucleophilic substitution using metal phosphides, (iv) Staudinger method, (v) hydrophosphination of , -unsaturated carbonyl compounds, (vi) Cu-and Pd-catalyzed C-P bond formation reactions, and (vii) reactions of cyclopalladated complexes with metal phosphides and HPPh2. Highlights of aminophosphine applications in asymmetric synthesis include their use in hydrogenation, hydrosilylation, and hydroboration reactions as well as in various transformations leading to a C-C bond formation such as Suzuki coupling, Meerwein-Eschenmoser-Claisen rearrangement, Mukaiyama aldol reaction, Tsuji allylation and ethylene oligomerization.ligands in a number of metal-catalyzed transformations are presented. Synthesis and applications of aminophosphines with a P-N bond are not included in this review. Preparation of -aminophosphoryl compounds [22] as well as reactions leading to the C-P bond formation using diphenylphosphine oxide HP(O)Ph 2 and dialkyl phosphites (RO) 2 P(O)H (see, for example, recent reports of Keglevich [23,24]) are also outside of the scope of this review. MAJOR CLASSES OF AMINOPHOSPHINES WITHOUT A P-N BONDThe majority of reported P,N-ligands without a P-N bond can be divided into several major categories (Chart 1). The first group is based on the ligands derived from ferrocene. Representatives of this group have been the first examples of chiral P,N-ligands successfully applied in asymmetric catalysis [25]. The second major group includes phosphino-oxazolines (PHOX), which are among the most successful catalysts in metal-catalyzed asymmetric reactions [6,7,[26][27][28][29][30][31][32]. The third group consists of chiral aliphatic P,Nligands, which can be obtained by a modification of a naturally available chiral source, e.g. amino acids [33,34]. The fourth group is formed by structurally diverse binaphthyl derivatives, so-called MAP ligands, which combine axial chirality with soft and hard coordination properties of phosphorus and nitrogen atoms [35]. The next group worth mentioning is represented by P,N-ligands with the pyridine or quinoline framework, e.g. QUINAP [8,36]. Representatives of the last type of aminophosphines have either phosphorusor nitrogen-containing non-aromatic heterocycle [37,38]. Separately from these major groups stand the ligands with structural features from two or more of the aforementioned ligand types, e.g. oxazoline-ferrocene [39] or pyrrolidine-MAP-derivatives [10]. SYNTHETIC APPROACHES TO AMINOPHOSPHINESDevelopment of synthetic routes to aminophosphines without a P-N bond recently received a lot of attention due to a growing number of impressive applications of these ligands in a...

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“…Activation of C–H bonds of substituted ferrocenes in the presence of stoichiometric or catalytic amounts of transition metals, e.g., palladium, ruthenium, or iridium, has been used for the synthesis of planar-chiral ferrocenes . Functionalized ferrocenes have been obtained by treatment with alkynes, alkenes, arenes, arylboronic acids, carbon monoxide, and phosphides . Gu, You, and co-workers, for example, converted ferrocene 53 into planar-chiral 1,2-disubstituted 268 in up to 99% ee by means of a palladium-catalyzed direct arylation with arylboronic acids (Scheme ) …”

Section: Miscellaneous Syntheses Of 12-disubstituted Ferrocenesmentioning

confidence: 99%

Selective Syntheses of Planar-Chiral Ferrocenes

2013

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Planar-chiral ferrocenes are widely applied in catalytic asymmetric transformations in scientific research as well as in industry. A plethora of different methodologies have been developed to access these molecules with a high degree of regio- and stereoselectivity. The aim of this contribution is to give a comprehensive overview of this topic. The synthesis of 1,2- and 1,3-substituted ferrocenes by electrophilic aromatic substitution, ortho-directed metalation, kinetic resolution, and desymmetrization is discussed. Advantages and disadvantages are highlighted.

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Optically active (2-aminomethylferrocenyl) phosphines with the phosphorus chiral center

Cited by 17 publications

References 11 publications

Chemoselectivity control in the reaction of a dinuclear chloro-bridged cyclopalladated complex with potassium diphenylphosphide

Chemoselectivity control in the reaction of a dinuclear chloro-bridged cyclopalladated complex with potassium diphenylphosphide

Synthesis of Aminophosphines and Their Applications in Catalysis

Selective Syntheses of Planar-Chiral Ferrocenes

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