Bismuth(III) nitrate pentahydrate: a convenient and selective reagent for conversion of thiocarbonyls to their carbonyl compounds

Mohammadpoor‐Baltork, Iraj; Khodaei, Mohammad Mehdi; Nikoofar, Kobra

doi:10.1016/s0040-4039(02)02516-9

Cited by 48 publications

(17 citation statements)

References 32 publications

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“…For example, Bi(NO 3 ) 3 ·5H 2 O and montmorillonite/Bi(NO 3 ) 3 have been used as the efficient nitrating reagents for conversion of phenolic compounds to nitrophenolic compounds [110], substituted anisoles to the corresponding nitro compounds [111], and for the ring opening of oxiranes and aziridines to form -(nitrooxy)-substituted alcohols and amines [112]. Bi(NO 3 ) 3 ·5H 2 O has also been described as a convenient and selective reagent for the conversion of thiocarbonyls to the corresponding carbonyl compounds [113].…”

Section: Bismuth-catalyzed Other Organic Reactionsmentioning

confidence: 99%

Recent Advances in Bismuth-Catalyzed Organic Synthesis

Hua

2008

COS

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Section: Bismuth-catalyzed Other Organic Reactionsmentioning

confidence: 99%

Recent Advances in Bismuth-Catalyzed Organic Synthesis

Hua

2008

COS

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“…Attempts to do the reaction using KMnO 4 in acidic acetone gave only decomposition products while Cl 2 /CCl 4 led to about 5% yield of the expected product starting from compound 2a. It was reported that treatment with Bi(NO 3 ) 3 gave good results in the transformation of thioamides into amides 17 but this methodology applied to 2a yielded only 30 % of 3a. TMS as an internal standard.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 5-(alkylthio or arylthio)-3H-1,2-dithiol-3-one derivatives

Fracaroli¹,

Kreiker²,

Rossi³

et al. 2006

Arkivoc

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“…[2] Notably,o ur procedure is also applicable to the synthesis of an ovel type of nitrogen-containing tricyclic molecular structure bearing an a-tetrasubstituted carbon stereocenter,w hich is an important structural motif in many biologically active natural alkaloids,s uch as hinckdentine A. [18] Therefore, treatment of 2a with excess Bi(NO 3 ) 3 ·(5 H 2 O) yielded the desired urea 5, [19] which was smoothly oxidized with [bis(trifluoroacetoxy)iodo]benzene (PIFA) into tricyclic amine 6 in 64 %yield without adecrease in the ee value (Scheme 3c). [20] In conclusion, we have developed the first highly enantioselective Brønsted acid catalyzed hydroamination of alkenes that provides access to av ariety of pyrrolidine derivatives with an a-tetrasubstituted carbon stereocenter with good to excellent yields and enantioselectivities under mild reaction conditions.Athiourea group that acts as both the activating and directing group is crucial for the hydroamination to proceed with high levels of stereoinduction by cooperative multiple hydrogen bonding with the Brønsted acid and the double bond.…”

Section: Methodsmentioning

confidence: 99%

Brønsted Acid Catalyzed Asymmetric Hydroamination of Alkenes: Synthesis of Pyrrolidines Bearing a Tetrasubstituted Carbon Stereocenter

et al. 2015

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The first highly enantioselective Brønsted acid catalyzedi ntramolecular hydroamination of alkenes enables the efficient construction of as eries of chiral (spirocyclic) pyrrolidines with an a-tetrasubstituted carbon stereocenter with excellent functional group tolerance.Aunique feature of this strategy is the use of at hiourea group acting as both the activating and the directing group through cooperative multiple hydrogen bonding with aB r ø nsted acid and the double bond. The utility of this method is highlighted by the facile construction of chiral synthetic intermediates and important structural motifs that are widely found in organic synthesis.Chiral amines bearing an a-tetrasubstituted carbon stereocenter are important structural motifs in numerous biologically active compounds and potent pharmaceutical agents. [1] Consequently,m ethods that enable their asymmetric construction are in great demand, [1,2] as this process still remains af ormidable synthetic challenge because of the difficulties associated with overcoming the steric hindrance and controlling the correct orientation of the four attached substituents. Recent years have witnessed as ignificant increase in the utilization of asymmetric intramolecular hydroamination reactions of alkenes as ah ighly valuable synthetic approach for the construction of chiral azaheterocycles with applications as biologically active compounds and powerful organocatalysts or ligands.[3] Numerous elegant metal-catalyzed asymmetric intramolecular olefin hydroaminations have been developed that either proceed by olefin activation through coordination to increase the electrophilicity of the olefin or by N À Hb ond activation to increase the nucleophilicity of the amine. [3,4] Despite these studies,amethod with which the more challenging hydroamination products that bear ac hiral quaternary center can be obtained with high enantioselectivity has not been reported to date. [5] On the other hand, unlike the well-established metalcatalyzed counterparts,t he organocatalytic hydroamination of alkenes still represents aformidable challenge.[3d,6] Thefirst enantioselective variant of this transformation, which involved the use of ac hiral phosphoric acid as the catalyst, resulted in poor stereocontrol with up to 17 % ee.[6a] However, only recently Toste et al. achieved asignificant breakthrough by using ad ithiophosphoric acid to enable the hydroamination of dienes and allenes.T heir approach involved the transient covalent attachment of achiral leaving group to the allylic system to obtain high enantioselectivities, [3d,6b] which was supported by the findingt hat the presence of the sulfur atom in the catalyst was necessary because the oxygenated analogues of the dithiophosphoric acid were less efficient. Alternatively,J acobsen and co-workers have developed asymmetric thiourea-catalyzed Cope-type alkene hydroamination reactions that proceed through dipolar transition states with multiple hydrogen bonding interactions.[6c] Although these pioneering reports provide str...

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Bismuth(III) nitrate pentahydrate: a convenient and selective reagent for conversion of thiocarbonyls to their carbonyl compounds

Cited by 48 publications

References 32 publications

Recent Advances in Bismuth-Catalyzed Organic Synthesis

Recent Advances in Bismuth-Catalyzed Organic Synthesis

Synthesis of 5-(alkylthio or arylthio)-3H-1,2-dithiol-3-one derivatives

Brønsted Acid Catalyzed Asymmetric Hydroamination of Alkenes: Synthesis of Pyrrolidines Bearing a Tetrasubstituted Carbon Stereocenter

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