Readily available chiral phosphine–aminophosphine ligands derived from 1-phenylethylamine for Rh-catalyzed enantioselective hydrogenations

Zhou, Xiaomao; Huang, Jia‐Di; Luo, Li‐Bin; Zhang, Chenglu; Zheng, Zhuo; Hu, Xiang‐Ping

doi:10.1016/j.tetasy.2010.03.008

Cited by 10 publications

(4 citation statements)

References 48 publications

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“…Bidentate phosphorus ligands were used as efficient catalysts in this type of reaction. The Xiao-Mao Zhou group transformed enantiomeric α-PEA to prepare a series of chiral phosphine-aminophosphine ligands ( Scheme 52 ) [ 76 ]. They used these ligands in the Rh-catalyzed asymmetric hydrogenation of olefins.…”

Section: Synthesis and Application Of Chiral Ligands With α-Pea Frmentioning

confidence: 99%

New Advances in the Synthetic Application of Enantiomeric 1-Phenylethylamine (α-PEA): Privileged Chiral Inducer and Auxiliary

Wosińska-Hrydczuk

Skarżewski

2020

Molecules

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New developments in the synthesis, resolution, and synthetic applications of chiral 1-phenylethylamine (α-PEA) reported in the last decade have been reviewed. In particular, improvements in the synthesis of α-PEA and its derivatives and chiral resolution, as well as their applications in the resolution of other compounds, were discussed. α-PEA was used as a chiral auxiliary in the diastereoselective synthesis of medicinal substances and natural products. Chiral ligands with α-PEA moieties were applied in asymmetric reactions, and effective modular chiral organocatalysts were constructed with α-PEA fragments and used in important synthetic reactions.

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Section: Synthesis and Application Of Chiral Ligands With α-Pea Frmentioning

confidence: 99%

New Advances in the Synthetic Application of Enantiomeric 1-Phenylethylamine (α-PEA): Privileged Chiral Inducer and Auxiliary

Wosińska-Hrydczuk

Skarżewski

2020

Molecules

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“…Such aminophosphines exhibit monodentate coordination with metals [14][15][16]. During the last decade it was shown that complexes of aminophosphines with a P-N bond can also exhibit significant catalytic activity in some transformations including hydrogenation [19,20] and Suzuki-Miyaura cross-coupling reactions [21]. During the last decade it was shown that complexes of aminophosphines with a P-N bond can also exhibit significant catalytic activity in some transformations including hydrogenation [19,20] and Suzuki-Miyaura cross-coupling reactions [21].…”

Section: Introductionmentioning

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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“…Thus, enantiopure o -hydroxybenzylamines have been employed as chiral ligands for asymmetric addition of dialkyl zinc reagents to aldehydes and in the enantioselective reduction of ketones, whereas o -methoxybenzylamines have been used in the design of highly efficient phosphoramidite ligands for Ir-catalyzed asymmetric allylic substitution reaction . Furthermore, chiral o -phosphinobenzylamines are useful bidentate ligands for enantioselective hydrogenation . Finally, o -aminobenzylamines have also been employed as efficient chiral catalysts and chiral reagents .…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Synthesis of 1,3-Diamines. II: Diastereoselective Reduction of AtropisomericN-tert-Butanesulfinylketimines

et al. 2011

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Readily available chiral phosphine–aminophosphine ligands derived from 1-phenylethylamine for Rh-catalyzed enantioselective hydrogenations

Cited by 10 publications

References 48 publications

New Advances in the Synthetic Application of Enantiomeric 1-Phenylethylamine (α-PEA): Privileged Chiral Inducer and Auxiliary

New Advances in the Synthetic Application of Enantiomeric 1-Phenylethylamine (α-PEA): Privileged Chiral Inducer and Auxiliary

Synthesis of Aminophosphines and Their Applications in Catalysis

Asymmetric Synthesis of 1,3-Diamines. II: Diastereoselective Reduction of AtropisomericN-tert-Butanesulfinylketimines

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