2018
DOI: 10.1021/jacs.8b11211
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Stereoretentive C(sp3)–S Cross-Coupling

Abstract: We report a stereoretentive cross-coupling reaction of configurationally stable nucleophiles with disulfide and N-sulfenylsuccinimide donors promoted by Cu­(I). We demonstrate the utility of this method in the synthesis of thioglycosides derived from simple alkyl and aryl thiols, thioglycosides, and in the glycodiversification of cysteine residues in peptides. These reactions operate well with carbohydrate substrates containing common protective groups and reagents with free hydroxyl and secondary amide functi… Show more

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Cited by 66 publications
(26 citation statements)
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“…This strategy, which represents an umpolung approach to glycodiversification, can be used in the preparation of (seleno)cysteine-modified peptides. 64,67,68 D. Peptide macrocyclization. Complementary to intermolecular transformations, we were intrigued by the possibility of engaging Ala Sn in cyclizations with properly functionalized electrophiles (Scheme 5A and 5B).…”
Section: A Ala M Acylationmentioning
confidence: 99%
See 1 more Smart Citation
“…This strategy, which represents an umpolung approach to glycodiversification, can be used in the preparation of (seleno)cysteine-modified peptides. 64,67,68 D. Peptide macrocyclization. Complementary to intermolecular transformations, we were intrigued by the possibility of engaging Ala Sn in cyclizations with properly functionalized electrophiles (Scheme 5A and 5B).…”
Section: A Ala M Acylationmentioning
confidence: 99%
“…In line with our interest in glycoconjugate synthesis via cross-coupling with anomeric nucleophiles, [64][65][66][67][68] we hypothesized that a stable stannane could be installed at the β carbon in alanine. Tetraalkylstannanes are generally considered poorly nucleophilic, but selective transfer of alkyl groups can be achieved using carbastannatranes [69][70][71][72][73] leading us to propose amino acids with the general formula Ala Sn 11 as competent reagents for umpolung functionalization.…”
Section: Introductionmentioning
confidence: 96%
“…In line with our interest in glycoconjugate synthesis via cross-coupling with anomeric nucleophiles, [61][62][63][64][65] we hypothesized that a stable stannane could be installed at the β carbon in alanine. Tetraalkylstannanes are generally considered poorly nucleophilic, but selective transfer of alkyl groups can be achieved using carbastannatranes 66, leading us to propose amino acids with the general formula Ala Sn 11 as competent reagents for umpolung functionalization.…”
Section: Introductionmentioning
confidence: 96%
“…This strategy, which represents an umpolung approach to glycodiversification, can be used in the preparation of (seleno)cysteine-modified peptides. 61,64,65 D. Peptide macrocyclization. Complementary to intermolecular transformations, we were intrigued by the possibility of engaging Ala Sn in cyclizations with properly functionalized electrophiles (Scheme 5A and 5B).…”
Section: Introductionmentioning
confidence: 99%