Palladium-catalyzed enantioselective allylation in the presence of phosphoramidites derived from (S a)-3-SiMe3-BINOL, (R,S)-semi-TADDOL, and (R,R)-TADDOL

Gavrilov, K. N.; Zheglov, Sergey V.; Novikov, I. M.; Chuchelkin, I. V.; Gavrilov, V. K.; Lugovsky, V. V.; Zamilatskov, Ilya A.

doi:10.1007/s11172-015-1047-7

Cited by 14 publications

(6 citation statements)

References 44 publications

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“…Enantioselectivities of up to 98% ee were obtained (see Scheme 3). With monodentate ligands L2, 65 L4, 60 and L5 61 the same levels of enantioselectivity were also achieved with pyrrolidine and sodium para-toluene sulfinate as nucleophiles. Bauer's group also studied other substrates using Pd−L8 as catalyst.…”

Section: Malonates Related Stabilized C-nucleophiles and O- S- N- And...mentioning

confidence: 73%

“…Stoltz and co-workers conceived a strategy for the catalytic enantioselective synthesis of (+)-eucomic acid (63) based on intermediate 64 as the carrier of the stereodefined tetrasubstituted α-hydroxyacid present in its structure. 497 present in other important natural products, such as (−)-aspterric acid methyl ester (65), quinic acid (66), and the harringtonine alkaloids (67), thus adding interest to the catalytic enantioselective preparation of this motif (Figure 22). For the preparation of intermediate 64, a Pd-catalyzed AAA reaction of 68 with 2-chloroallyl mesylate using PHOX ligand (S)-L122 was envisaged (Scheme 172).…”

Section: Application In Total Synthesismentioning

confidence: 99%

“…Among the monodentate P-donor ligands developed since 2008 for Pd-catalyzed asymmetric allylic alkylation (AAA), diamidophosphites − and phosphoramidites − were found to provide higher enantioselectivities than their phosphite, , phosphinite, and phosphine − counterparts. Scheme collects the most representative families of monodentate P-donor ligands evaluated in the allylic alkylation of rac -1,3-diphenylallyl acetate as substrate with dimethyl malonate as nucleophile.…”

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.

410

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: Malonates Related Stabilized C-nucleophiles and O- S- N- And...mentioning

confidence: 73%

Section: Application In Total Synthesismentioning

confidence: 99%

Section: Asymmetric Allylic Substitutionmentioning

confidence: 99%

See 1 more Smart Citation

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

Pàmies

Margalef

Cañellas³

et al. 2021

Chem. Rev.

410

202

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“…We tested skewedness of the data using Spearman’s rank correlation tests and the Jarque–Bera normtest ( Jarque & Bera, 1987 ; Gavrilov & Pusev, 2015 ).…”

Section: Methodsmentioning

confidence: 99%

Wild meat hunting and use by sedentarised Baka Pygmies in southeastern Cameroon

Martin¹,

Brull²,

Funk

et al. 2020

PeerJ

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As a result of sedentarisation many Baka Pygmies have changed their mobility patterns away from nomadic lifestyles to living in roadside villages. These settled groups are increasingly dependent on cultivated foods but still rely on forest resources. The level of dependence on hunting of wild animals for food and cash, as well as the hunting profiles of sedentarised Pygmy groups is little known. In this study we describe the use of wild meat in 10 Baka villages along the Djoum-Mintom road in southeastern Cameroon. From data collected from 1,946 hunting trips by 121 hunters, we show that most trips are of around 13 hours and a median of eight hours. A mean ± SD of 1.15 ± 1.11 animal carcasses are taken in a single trip; there was a positive correlation between duration of trips and carcasses. A total of 2,245 carcasses of 49 species of 24 animal families were taken in the study; species diversity was similar in all villages except one. Most hunted animals were mammals, with ungulates contributing the highest proportion. By species, just over half of the animal biomass extracted by all hunters in the studied villages was provided by four mammal species. Most animals were trapped (65.77% ± 16.63), followed by shot with guns (22.56% ± 17.72), other methods (8.69% ± 6.96) and with dogs (2.96% ± 4.49). A mean of 7,569.7 ± 6,103.4 kg yr−1 (2,080.8–19,351.4) were extracted per village, giving 75,697 kg yr−1 in total, which is equivalent to 123 UK dairy cattle. In all villages, 48.07% ± 17.58 of animals hunted were consumed by the hunter and his family, around 32.73% ± 12.55, were sold, followed by a lower percentage of carcasses partially sold and consumed (19.21% ± 17.02). Between 60% and 80% of carcasses belonged to the “least concern” category, followed by “near threatened”, “vulnerable” and, rarely “endangered”. The only endangered species hunted was the chimpanzee (Pan troglodytes). We suggest that hunting is a critical activity that provides a vital source of food for our study communities. Measured wild meat extraction levels are likely to be sustainable if hunter densities do not increase.

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“…[22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] We have previously reported the preparation of a series of chiral ligands -phosphorous acid derivatives, which were successfully applied in Pd-catalyzed allyl substitution reactions. [38][39][40][41][42][43] In those cases, porphyrins were used both as achiral additives [38][39][40][41] to increase enantioselectivity, and as starting substrates for phosphorylation. [42][43][44] In a preliminary communication, [44] we reported the synthesis of the first tetradentate diamidophosphite 1 (Figure 1) and its application in asymmetric Pd-catalyzed alkylation of cinnamyl acetate.…”

Section: Introductionmentioning

confidence: 99%

First Tetradentate Diamidophosphite Based on [5,10,15,20-Tetrakis(4-hydroxyphenyl)porphyrinato]zinc: Synthesis, Spectral Features, Coordination, and Application in Asymmetric Pd-Catalyzed Reactions

Mikhel¹,

Gavrilov²,

Zheglov³

et al. 2021

MHC

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The synthesis of the tetradentate diamidophosphite (L) containing four 1,3,2-diazaphospholidine rings and a porphyrin moiety, its characterization and application in asymmetric Pd-catalyzed reactions are reported. The best results (up to 63 % ee) were obtained for the Pd-catalyzed allylic alkylation of (E)-1,3-diphenylallyl acetate with dimethylmalonate. The complex L[Ru(p-cymene)Cl 2 ] 4 was synthesized in situ and characterized by spectroscopic data. The structure of the compounds obtained is discussed based on 1

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Palladium-catalyzed enantioselective allylation in the presence of phosphoramidites derived from (S a)-3-SiMe3-BINOL, (R,S)-semi-TADDOL, and (R,R)-TADDOL

Cited by 14 publications

References 44 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

Wild meat hunting and use by sedentarised Baka Pygmies in southeastern Cameroon

First Tetradentate Diamidophosphite Based on [5,10,15,20-Tetrakis(4-hydroxyphenyl)porphyrinato]zinc: Synthesis, Spectral Features, Coordination, and Application in Asymmetric Pd-Catalyzed Reactions

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