2018
DOI: 10.1002/chem.201706167
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Catalytic Enantioselective Synthesis of Highly Functionalized Pentafluorosulfanylated Pyrrolidines

Abstract: The first catalytic asymmetric synthesis of highly functionalized pentafluorosulfanylated pyrrolidines is described. The method, based on a 1,3-dipolar cycloaddition reaction of aryl and heteroaryl-substituted glycine Schiff bases with pentafluorosulfanyl acrylic esters, gave access to a broad range of pyrrolidines bearing aryl, naphtyl, and heteroaryl groups. By using Xing-Phos as a catalyst, the corresponding products were obtained in good yields, good to high regioselectivity, and excellent diastereo- and e… Show more

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Cited by 18 publications
(10 citation statements)
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“…In particular for aliphatic imine 2c with a branched i -Pr group, higher yield (70%) and better enantioselectivity (97% ee) than that for linear aliphatic imines were observed. This result supported the magic effect of the multiple stereogenic substituents on syn -( R, R s )-Xing-Phos , in the silver-mediated AYI cycloaddition reactions under conditions A. Notably, the stereochemical and configuration assignment of syn - 3ag was determined by X-ray analysis (Figure ) in which the structure of syn -products 3 was further confirmed with good syn -selectivity in this Xing-Phos-controlled AYI cycloaddition reaction.…”
supporting
confidence: 70%
“…In particular for aliphatic imine 2c with a branched i -Pr group, higher yield (70%) and better enantioselectivity (97% ee) than that for linear aliphatic imines were observed. This result supported the magic effect of the multiple stereogenic substituents on syn -( R, R s )-Xing-Phos , in the silver-mediated AYI cycloaddition reactions under conditions A. Notably, the stereochemical and configuration assignment of syn - 3ag was determined by X-ray analysis (Figure ) in which the structure of syn -products 3 was further confirmed with good syn -selectivity in this Xing-Phos-controlled AYI cycloaddition reaction.…”
supporting
confidence: 70%
“…Scheme 22 Catalytic enantioselective synthesis of SF5-pyrrolidines 25 Indoles represent one of the most widely used classes of heterocyclic compounds in medicinal chemistry. Bizet et al described an efficient and scalable strategy to access 2-SF5 (aza)indoles.…”
Section: Synthesis Of Sf5/sf4cl/sf4-substituted Small Molecules Heter...mentioning
confidence: 99%
“…Notably, Xing-Phos has been proved to be highly efficient in promoting the asymmetric cycloaddition of glycine aldimino esters with various activated alkenes (Scheme ), ,, including nitroalkenes, maleimides, chalcones, and less-reactive methyl cinnamates, giving the corresponding enantioenriched pyrrolidines with multiple stereogenic centers in good yields and diastereoselectivities (up to >98:2 dr) as well as excellent enantioselectivities (up to 99% ee). Recently, Jubault, Bouillon, and co-workers also revealed the excellent performance of Xing-Phos in the catalytic asymmetric synthesis of highly functionalized pentafluorosulfanyl (SF 5 )-substituted pyrrolidines (up to 98% ee) …”
Section: Enantioselective Construction Of Multiple Stereogenic Centersmentioning
confidence: 99%