76403-21-9Relevant academic research and scientific papers
Copper-Catalyzed Amino Lactonization and Amino Oxygenation of Alkenes Using O-Benzoylhydroxylamines
Hemric, Brett N.,Shen, Kun,Wang, Qiu
supporting information, p. 5813 - 5816 (2016/06/09)
A copper-catalyzed amino lactonization of unsaturated carboxylic acids has been achieved as well as the analogous intermolecular three-component amino oxygenation of olefins. The transformation features mild conditions and a remarkably broad substrate sco
Platinum(IV)-Catalyzed Synthesis of Unsymmetrical Polysubstituted Benzenes via Intramolecular Cycloaromatization Reaction
Zheng, Shuyan,Zhang, Jinghua,Shen, Zhengwu
supporting information, p. 2803 - 2808 (2015/09/28)
A one-pot synthesis of polysubstituted benzene derivatives was achieved via a platinum(IV)-catalyzed intramolecular cycloaromatization reaction. The reaction proceeds via a tandem skeletal rearrangment, dehydration and double bond isomerization, which proved to be very useful for the syntheses of a range of interesting polyalkyl-substituted benzenes.
Kinetic resolution of racemic carboxylic acids through asymmetric protolactonization promoted by chiral phosphonous acid diester
Sakuma, Masayuki,Sakakura, Akira,Ishihara, Kazuaki
supporting information, p. 2838 - 2841 (2013/07/19)
Chiral phosphonium salts induce the kinetic resolution of racemic α-substituted unsaturated carboxylic acids through asymmetric protolactonization. Both the lactones and the recovered carboxylic acids are obtained with high enantioselectivities and high S
Highly enantioselective direct alkylation of arylacetic acids with chiral lithium amides as traceless auxiliaries
Stivala, Craig E.,Zakarian, Armen
supporting information; experimental part, p. 11936 - 11939 (2011/09/19)
A direct, highly enantioselective alkylation of arylacetic acids via enediolates using a readily available chiral lithium amide as a stereodirecting reagent has been developed. This approach circumvents the traditional attachment and removal of chiral auxiliaries used currently for this type of transformation. The protocol is operationally simple, and the chiral reagent is readily recoverable.
Regioselective silver-mediated Kondakov-Darzens olefin acylation
Barczak, Nicholas T.,Jarvo, Elizabeth R.
supporting information; experimental part, p. 12912 - 12916 (2011/12/04)
Enone construction: A silver-mediated olefin acylation reaction is described, in which five-, six-, and -seven-membered rings, tetrasubstituted olefins, bridged bicycles, spirocycles, and benzoxepinones are prepared. Highly selective intermolecular reactions are coupled to a Nazarov cyclization for the effective preparation of cyclopentenones, including the core of modhephene (see scheme). Copyright
Ligand effects on dirhodium(II) carbene reactivities. Highly effective switching between competitive carbenoid transformations
Padwa, Albert,Austin, David J.,Price, Alan T.,Semones, Mark A.,Doyle, Michael P.,Protopopova, Marina N.,Winchester, William R.,Tran, Andrea
, p. 8669 - 8680 (2007/10/02)
Carboxylate and carboxamide ligands of dirhodium(II) catalysts control chemoselectivity in competitive metal carbene transformations of diazo compounds. For competitive intramolecular cyclopropanation versus intramolecular aromatic substitution with 1-diazo-3-aryl-5-hexen-2-ones, use of Rh2(OAc)4 results in the products from both transformations in nearly equal amounts, but dirhodium(II) perfluorobutyrate (Rh2(pfb)4) provides only the aromatic substitution product while dirhodium(II) caprolactamate (Rh2(cap)4) gives only the cyclopropanation product. Similar results are obtained from dirhodium(II) catalysts in competitive intramolecular cyclopropanation versus tertiary C-H insertion, aromatic cycloaddition versus C-H insertion, cyclopropanation versus aromatic cycloaddition, and C-H insertion versus aromatic substitution. The order of reactivity for metal carbenes generated from Rh2(pfb)4 is aromatic substitution > tertiary C-H insertion > cyclopropanation ~ aromatic cycloaddition > secondary C-H insertion, and the rate differences between them are as much as 100-fold. For Rh2(cap)4 the order of reactivity is cyclopropanation > tertiary C-H insertion > secondary C-H insertion > aromatic cycloaddition with aromatic substitution not observed as a competing process for the diazo compounds examined. Control of chemoselectivity through charge and/or frontier molecular orbital properties of the intermediate metal carbene has been evaluated. Competitive product formation from dirhodium(II) caprolactamate catalyzed reactions of N-tert-butyl-N-benzyldiazoacetoacetamide is temperature dependent over a narrow 15-deg range. The effect of carbene substituents other than the ligated dirhodium(II) on chemoselectivity is described and discussed.
An Efficient and General Synthesis of 5-Substituted Pyrrolidinones
Miller, R. D.,Goelitz, P.
, p. 1616 - 1618 (2007/10/02)
2-Pyrrolidinone derivatives are widespread materials of considerable laboratory and commercial importance.In spite of this, there is no generally useful synthesis of either symmetrically or unsymmetrically 5,5-disubstituted derivatives.This is particularl
