New phosphine-imine and phosphine-amine ligands derived from  d -gluco-,  d -galacto- and  d -allosamine in Pd-catalysed asymmetric allylic alkylation

Szulc, Izabela; Kołodziuk, Robert; Zawisza, A.

doi:10.1016/j.tet.2018.02.009

Cited by 5 publications

(5 citation statements)

References 113 publications

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“… 236 , 240 For instance, enantioselectivities of up to >99% ee were described with the phosphine-imino ligand L70 derived from d -glucosamine. 240 …”

Section: Asymmetric Allylic Substitutionmentioning

confidence: 99%

“…259 Excellent enantioselectivities were also induced by phosphine-imino ligands with a chiral imine group. 236,240 For instance, enantioselectivities of up to >99% ee were described with the phosphine-imino ligand L70 derived from Dglucosamine. 240 Pyridine/quinoline-based heterodonor P,N-ligands have also been used extensively.…”

Section: T H Imentioning

confidence: 99%

“…236,240 For instance, enantioselectivities of up to >99% ee were described with the phosphine-imino ligand L70 derived from Dglucosamine. 240 Pyridine/quinoline-based heterodonor P,N-ligands have also been used extensively. 241−248 For example, Jiang's group successfully applied the [2,2]-paracyclophane-derived phosphine-quinoline ligand L71 in the allylic alkylation of rac-1,3diphenylallyl acetate with dimethyl malonate (ee values up to 99%).…”

Section: T H Imentioning

confidence: 99%

“…The interest in this kind of ligand for Pd-catalyzed allylic substitution continues to be spurred by the early success of the Pd-PHOX catalytic system. Albeit the field is still dominated by P-oxazoline ligands, ,,− other ligands, such as P-iminos, − P-pyridine/quinolines, − and others, − are increasingly studied. Figure collects the most successful classes of new P-oxazoline ligands and other new P,N(sp 2 )-ligands.…”

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.

411

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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“… 236 , 240 For instance, enantioselectivities of up to >99% ee were described with the phosphine-imino ligand L70 derived from d -glucosamine. 240 …”

Section: Asymmetric Allylic Substitutionmentioning

confidence: 99%

Section: T H Imentioning

confidence: 99%

Section: T H Imentioning

confidence: 99%

Section: Asymmetric Allylic Substitutionmentioning

confidence: 99%

See 2 more Smart Citations

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

Pàmies

Margalef

Cañellas³

et al. 2021

Chem. Rev.

411

202

View full text Add to dashboard Cite

show abstract

“…Chiral aziridines are useful intermediates in the synthesis of biologically significant compounds due to their ability to undergo nucleophilic ring opening reactions [ 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 ]. Considering our previous results on carbohydrate chemistry [ 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 ] and based on our experience in synthesis and catalytic activity in the asymmetric synthesis of chiral aziridines [ 59 , 60 , 61 , 62 , 63 , 64 , 65 ], we decided to couple aziridines to glycals with D-gluco and D-galacto configurations via C -glycosidic bonding, with the final formation of C -glycosyl-aminoethyl sulfide derivatives.…”

Section: Introductionmentioning

confidence: 99%