P∗,P∗-Bidentate diastereoisomeric bisdiamidophosphites based on N-benzyltartarimide and their applications in asymmetric catalytic processes

Gavrilov, K. N.; Zheglov, Sergey V.; Benetsky, Eduard B.; Safronov, A. S.; Rastorguev, E. A.; Groshkin, Nikolay N.; Davankov, V. A.; Schäffner, Benjamín; Börner, Armin

doi:10.1016/j.tetasy.2009.10.022

Cited by 16 publications

(8 citation statements)

References 46 publications

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“…A range of phosphinites, , diphosphoramidites, diphosphites, − and bisdiamidophosphites − were also applied as ligands. High enantioselectivities were mainly achieved in the alkylation of 1,3-diphenylallyl acetate using malonates (Scheme a).…”

Section: Asymmetric Allylic Substitutionmentioning

confidence: 99%

“…Gavrilov and co-workers have shown the benefit of using bisdiamidophosphites with diazaphospholididene rings, providing enantioselectivities of >90% ee in the allylic alkylation of 1,3-diphenylallyl acetate with dimethyl malonate regardless of the ligand backbone used. − ,− Among them, ligands L41 and L42 are highlighted for the excellent ee values induced in reactions with primary and secondary alkyl amines and sodium para -toluenesulfinate . However, ee values clearly decreased with less hindered substrates like cyclohexenyl carbonates or esters. , In contrast, the resorcinol-based P-stereogenic bisdiamidophosphite L43 provided 92% ee in the allylic alkylation of cyclohex-2-enyl ethyl carbonate with dimethyl malonate (Scheme b) …”

Section: Asymmetric Allylic Substitutionmentioning

confidence: 99%

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Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications

Pàmies

Margalef

Cañellas³

et al. 2021

Chem. Rev.

369

202

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This Review compiles the evolution, mechanistic understanding, and more recent advances in enantioselective Pd-catalyzed allylic substitution and decarboxylative and oxidative allylic substitutions. For each reaction, the catalytic data, as well as examples of their application to the synthesis of more complex molecules, are collected. Sections in which we discuss key mechanistic aspects for high selectivity and a comparison with other metals (with advantages and disadvantages) are also included. For Pd-catalyzed asymmetric allylic substitution, the catalytic data are grouped according to the type of nucleophile employed. Because of the prominent position of the use of stabilized carbon nucleophiles and heteronucleophiles, many chiral ligands have been developed. To better compare the results, they are presented grouped by ligand types. Pd-catalyzed asymmetric decarboxylative reactions are mainly promoted by PHOX or Trost ligands, which justifies organizing this section in chronological order. For asymmetric oxidative allylic substitution the results are grouped according to the type of nucleophile used.

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Section: Asymmetric Allylic Substitutionmentioning

confidence: 99%

Section: Asymmetric Allylic Substitutionmentioning

confidence: 99%

Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications

Pàmies

Margalef

Cañellas³

et al. 2021

Chem. Rev.

369

202

View full text Add to dashboard Cite

show abstract

“…Gavrilov and co-workers prepared chiral diphosphite analogues of catASium M [28] by reaction of chlorodiamidophosphites with 3,4-dihydroxy-N-benzyltartarimide, as depicted in Scheme 12. [44,45] Diastereomers have been separated by flash chromatography on a multigram-scale.…”

Section: Bidentate C 2 -Symmetric Ligandsmentioning

confidence: 99%

The Synthesis of Chiral Phosphorus Ligands for use in Homogeneous Metal Catalysis

2011

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Recent developments in the synthesis of chiral phosphorus ligands are summarized. Main emphasis is given to the multitude of protocols for their synthesis starting from compounds of the chiral pool or by using other easily available chiral starting materials. Besides mono-and bidentate P-ligands hybrid ligands bearing N, O, or olefinic groups as second ligating units are addressed. The syntheses of new P-chirogenic ligands, as well as ligands with supramolecular structures are likewise reviewed. In appropriate cases structures of related privileged ligands are given for comparison. When available, the efficiency of the new ligands for metal catalyzed reactions are briefly assessed.[a] Dr.

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“…P-chiral ligands have been less frequently applied in catalysis. Recently, asymmetric bis-diamidophosphites L31 and L32 have been prepared [60,61], with promising results (Fig. 7).…”

Section: P-chiral Ligandsmentioning

confidence: 99%

Palladium-Catalyzed Enantioselective Allylic Substitution

Milhau

Guiry

2011

Topics in Organometallic Chemistry

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Palladium-catalyzed allylic substitution is one of the main reactions for testing new chiral ligands. The most relevant examples from the work published in the period 2007 to mid-2010 are reviewed. The vast majority of the work published within this timeframe relies upon the application of chiral ligands for asymmetric induction. The recent advances in the development and applications of new chiral P-P, P-N, P-O, P-S, N-N, N-S, S-S, and NHC ligands are covered and are the main focus of this chapter. Other aspects of enantioselective palladium allylic alkylations are discussed in the subsequent sections, for example, heterogeneous catalysis, the use of chiral salt additives, and recent applications in kinetic resolution.

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P∗,P∗-Bidentate diastereoisomeric bisdiamidophosphites based on N-benzyltartarimide and their applications in asymmetric catalytic processes

Cited by 16 publications

References 46 publications

Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications

Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications

The Synthesis of Chiral Phosphorus Ligands for use in Homogeneous Metal Catalysis

Palladium-Catalyzed Enantioselective Allylic Substitution

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