1229648-97-8Relevant articles and documents
Unified Approach to Fused and Spirocyclic Oxindoles through Lewis-Acid-Promoted Opening of Spiroepoxyoxindoles with Allylsilanes: Application to the Formal Synthesis of (±)-Physovenine
Sharma, Brijesh M.,Yadav, Mahesh,Gonnade, Rajesh G.,Kumar, Pradeep
, p. 2603 - 2609 (2017)
A protocol for the construction of oxindoles containing all-carbon quaternary centres in a highly regioselective manner has been developed. The reaction involves opening of spiroepoxyoxindoles with allylsilanes to give Hosomi–Sakurai-type products as well as new silicon-containing spirocyclic oxindoles. A formal synthesis of (±)-physovenine was accomplished in five steps using this protocol.
Candida antarctica lipase-B-catalyzed kinetic resolution of 1,3-dialkyl-3-hydroxymethyl oxindoles
Kumar, Naveen,Kumar, Akshay,Sahoo, Subash Chandra,Chimni, Swapandeep Singh
, p. 1377 - 1394 (2020/11/23)
Candida antarctica (CAL-B) lipase-catalyzed resolution of 1,3-dialkyl-3-hydroxymethyl oxindoles has been performed to obtain (R)-1,3-dialkyl-3-acetoxymethyl oxindoles with up to 99% ee and (S)-1,3-dialkyl-3-hydroxymethyl oxindoles with up to 78% ee using vinyl acetate as acylating agent and acetonitrile as solvent transforming (S)-3-allyl-3-hydroxymethyl oxindole to (3S)-1′-benzyl-5-(iodomethyl)-4,5-dihydro-2H-spiro[furan-3,3′-indolin]-2′-one. The optically active 3-substituted-3-hydroxymethyl oxindoles and spiro-oxindoles are among the key synthons in the synthesis of potentially biologically active molecules.
Reversal of Selectivity in C3-Allylation and Formal [3 + 2]-Cycloaddition of Spiro-epoxyoxindole: Unified Synthesis of Spiro-furanooxindole, (±)-N-Methylcoerulescine, (±)-Physovenine, and 3a-Allylhexahydropyrrolo[2,3-b]indole
Hajra, Saumen,Roy, Sayan,Maity, Subrata
supporting information, p. 1998 - 2001 (2017/04/28)
An effective Lewis acid catalyzed regioselective C3-allylation and a formal [3 + 2]-annulation reaction of spiro-epoxyoxindoles have been developed and can be accessed simply by changing the reaction conditions. This method has been successfully employed for the synthesis of spiro(pyrrolidinyloxindole), 3a-allylhexahydropyrrolo[2,3-b]indole, and furanoindoline.
Applications of NHC-mediated O- to C-carboxyl transfer: synthesis of (±)-N-benzyl-coerulescine and (±)-horsfiline
Thomson, Jennifer E.,Kyle, Andrew F.,Ling, Kenneth B.,Smith, Siobhan R.,Slawin, Alexandra M.Z.,Smith, Andrew D.
experimental part, p. 3801 - 3813 (2010/07/02)
NHC-promoted O- to C-carboxyl transfer of 3-allyl indolyl phenyl carbonates generates 3-allyl-3-phenoxycarbonyl-oxindoles with good catalytic efficiency, which are readily converted into (±)-N-benzyl-coerulescine and (±)-horsfiline.
