2019
DOI: 10.1002/anie.201814074
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Catalytic Enantioselective Ynamide Additions to Isatins: Concise Access to Oxindole Alkaloids

Abstract: The highly enantioselective addition of terminal ynamides to av ariety of isatins,c atalyzedbyabisoxazolidine copper complex under mild, base-free reaction conditions,i s described. The reaction is broad in scope,scalable,applicable to unprotected isatins,a nd provides efficient access to 3hydroxyoxindoles carrying atetrasubstituted chiral center with excellent yields and enantioselectivities.Synthetically versatile, multifunctional 3-hydroxyindolinones are obtained by hydration, partial hydrogenation, or hydr… Show more

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Cited by 34 publications
(12 citation statements)
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“…Thep resent protocol offers new opportunities for the development of novel reactions of ynamides,especially those based on asymmetric catalysis. [23]…”
Section: Resultsmentioning
confidence: 99%
“…Thep resent protocol offers new opportunities for the development of novel reactions of ynamides,especially those based on asymmetric catalysis. [23]…”
Section: Resultsmentioning
confidence: 99%
“…However, compared with asymmetric alkynylation of aldehydes, [4d, 5] efficient catalytic systems for alkynylation of ketones [6] to generate propargylic alcohols with tetrasubstituted stereogenic centers remain underdeveloped, largely because of the low reactivity of metalated terminal alkynes toward ketones. For enantioselective alkynylation of isatins, [7–9] efficient catalytic systems, such as CuI/chiral guanidine, CuI/chiral phosphine ligand, Zn(OTf) 2 /chiral hydroxyl oxazoline ligand, AgOAc/chiral phase‐transfer catalyst, CuOTf/bisoxazolidine, and Co(OAc) 2 /bisoxazolinephosphine have been developed by the groups of Liu, [7a] Guo, [7b] Chen, [7c] Maruoka, [7d] Wolf, [7e] and Li, [7f] respectively. 3‐Alkynyl‐3‐hydroxy‐2‐oxindoles generated by alkynylation of isatins have been found to exhibit important biological activities (Scheme 1 b).…”
Section: Methodsmentioning
confidence: 99%
“…As depicted in Scheme , the reactions were conducted in the presence of 5 mol % of Cu­(OTf) 2 and 5 mol % of bisoxazolidine 36 , giving multifunctional 3-hydroxyoxindoles 37 in 75–99% yields and 89–99% ee values (Scheme ). The synthetic value of product 37e was vividly demonstrated by the two-step synthesis of cinchonamidine alkaloid 39 with no loss in enantiopurity via a Pd/C-catalyzed hydrogenation and Mg/MeOH-mediated detosylative cyclization sequence. The present protocol compares favorably with literature precedents on asymmetric chimonamidine synthesis.…”
Section: Alkynylation Reactionmentioning
confidence: 99%