- Highly diastereoselective synthesis of tetralin-fused spirooxindoles via lewis acid-catalyzed C(sp3)H bond functionalization
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A highly diastereoselective synthesis of tetralin-fused spirooxindole derivatives was described. Treatment of benzylidene oxindoles with a catalytic amount of Sc(OTf)3 in refluxing hexane afforded the target compounds in good chemical yields with excellent diastereoselectivities (up to >20:1). Detailed investigation of the reaction mechanism revealed that both interconversion of the two diastereomers and their solubility difference in reaction medium were the key to achieving excellent diastereoselectivities.
- Machida, Mizuki,Mori, Keiji
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supporting information
p. 868 - 871
(2018/07/03)
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- Chiral Magnesium Bisphosphate-Catalyzed Asymmetric Double C(sp3)-H Bond Functionalization Based on Sequential Hydride Shift/Cyclization Process
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Described herein is a chiral magnesium bisphosphate-catalyzed asymmetric double C(sp3)-H bond functionalization triggered by a sequential hydride shift/cyclization process. This reaction consists of stereoselective domino C(sp3)-H bond functionalization: (1) a highly enantio- and diastereoselective C(sp3)-H bond functionalization by chiral magnesium bisphosphate (first [1,5]-hydride shift), and (2) a highly diastereoselective C(sp3)-H bond functionalization by an achiral catalyst (Yb(OTf)3, second [1,5]-hydride shift).
- Mori, Keiji,Isogai, Ryo,Kamei, Yuto,Yamanaka, Masahiro,Akiyama, Takahiko
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supporting information
p. 6203 - 6207
(2018/05/23)
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- Construction of 1,3-Dithio-Substituted Tetralins by [1,5]-Alkylthio Group Transfer Mediated Skeletal Rearrangement
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A novel skeletal rearrangement involving a [1,5]-alkylthio group transfer/cyclization sequence is described. Treatment of benzylidene malonates having a thioketal moiety at the homobenzyl position with a catalytic amount of Sc(OTf)3 afforded alkylthio group rearranged adducts in good chemical yields. Detailed investigation of the reaction mechanism revealed that an intramolecular conjugate addition/ring opening sequence (not through-space transfer) is the key to achieving this reaction.
- Hisano, Naoya,Kamei, Yuto,Kansaku, Yaoki,Yamanaka, Masahiro,Mori, Keiji
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supporting information
p. 4223 - 4226
(2018/07/29)
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- Gold-catalyzed 1,2-oxoarylations of nitriles with pyridine-derived oxides
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We report the first success in the gold-catalyzed oxoarylations of nitriles with pyridine-derived N-oxides using gold carbenes as initiators. These oxoarylations were also achieved satisfactorily in intermolecular three-component oxidations, including diverse alkenyldiazo esters, nitriles, and pyridine-based oxides. Spill the (car)benes: Reported herein is the first successful gold-catalyzed oxoarylation of nitriles with pyridine-derived N-oxides using gold carbenes as initiators (see scheme; DCE=1,2-dichloroethane, IPr=1,3-bis(diisopropylphenyl)imidazol-2-ylidene). These oxoarylations were also achieved satisfactorily in intermolecular three-component oxidations using a variety of alkenyldiazo esters, nitriles, and pyridine-based N-oxides.
- Karad, Somnath Narayan,Liu, Rai-Shung
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supporting information
p. 5444 - 5448
(2014/06/09)
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- Synthesis of N-alkoxyindol-2-ones by copper-catalyzed intramolecular N-arylation of hydroxamates
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The first example of copper-catalyzed intramolecular N-arylation of hydroxamic acid derivatives is presented. Based on this transformation a new method for the synthesis of N-alkoxyindol-2-ones from 2-(2-bromoaryl) acetylhydroxamates has been developed. T
- Kukosha, Tatyana,Trufilkina, Nadezhda,Katkevics, Martins
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supporting information; experimental part
p. 2525 - 2528
(2011/11/13)
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- Polysubstituted derivatives of 10-piperazinodibenzo (b,f) thiepine
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Polysubstituted derivatives of 10-piperazinodibenzo (b,f) thiepine and processes for the preparation thereof are described. The compositions evidence psychotropic and antimicrobial characteristics and are of low toxicity. The described compounds are of the general formula STR1 wherein R2, R3, R7 and R8 are selected from among hydrogen, fluorine and chlorine atoms, a fluoromethyl group, a methoxy group and a hydroxyl group, at least three of R2, R3, R7 and R8 being other than hydrogen, R being selected from among hydrogen, alkyl or alkylhydroxy groups having from 1-3 carbon atoms, an acyloxyalkyl group having from 8-10 carbon atoms in the acyl moiety and from 2-3 carbon atoms in the alkyl moiety and an ethoxycarbonyl group, m and n representing integers from 0-1 and the bond between the 10 and 11 carbon atoms being either a single or double bond.
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