2019
DOI: 10.1021/acs.orglett.9b02228
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Gold(I)-Catalyzed Synthesis of Furopyrans: Insight into Hetero-Diels–Alder Reactions

Abstract: We report herein the synthesis of complex molecules containing furopyran cores through a gold(I)-catalyzed hetero Diels-Alder cascade reaction. During this process, the diene and the dienophile are produced concomitantly by the action of a single catalyst from a single starting material. Moreover, six bonds, four heterocycles and four controlled stereogenic centers are formed in a one-step operation. DFT calculations provide the mechanistic basis of this unprecedented reaction.

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Cited by 14 publications
(16 citation statements)
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“…Intermediate C undergoes protodeauration to generate the oxocine-fused indole 2 . Alternatively, elimination of gold from intermediate D may occur to provide allene 4 , which is converted to the propellane-type indoline 3 , as we reported previously . The reverse reaction of allene 4 to vinyl-gold C should be much slower than the formation of G because the reaction of 4a produced only a small amount of 2a under condition A (4%, Scheme ).…”
Section: Resultsmentioning
confidence: 82%
“…Intermediate C undergoes protodeauration to generate the oxocine-fused indole 2 . Alternatively, elimination of gold from intermediate D may occur to provide allene 4 , which is converted to the propellane-type indoline 3 , as we reported previously . The reverse reaction of allene 4 to vinyl-gold C should be much slower than the formation of G because the reaction of 4a produced only a small amount of 2a under condition A (4%, Scheme ).…”
Section: Resultsmentioning
confidence: 82%
“…These results show that the specific nucleophilicity of the heteroatoms involved, induces different reactivities of the substrates. Indeed, whereas in the case of phenol ether derivatives recently described by us, [9a–c] the process starts with the intramolecular 5‐ endo ‐dig hydroalkoxylation, the more nucleophilic anilines and thioethers counterparts attack first the gold‐activated triple bond of the butynol moiety leading respectively to an indole [8] or a benzothiophene via intramolecular 5‐ endo ‐dig carboamination or carbothiolation (Figure 2).…”
Section: Resultsmentioning
confidence: 99%
“…To set up a reliable computational model for the reaction, 1‐Me ( Scheme 2) was used as model substrate 1 and (2‐biphenyl)‐dimethylphosphine (MeJohnPhos) as a model ligand for the cationic gold complex [49,50] . Scheme 2 shows the reaction profile for the ammoniumation reaction followed by nucleophilic substitution of the (2‐alkynyl)phenylsulfonyl azetidine 1‐Me in the presence of the gold catalyst.…”
Section: Resultsmentioning
confidence: 99%