Stereoselective hydrostannation of substituted alkynes with trineophyltin hydride

Dodero, Verónica Isabel; Koll, Liliana C.; Mandolesi, Sandra D.; Podestá, Julio C.

doi:10.1016/s0022-328x(02)01213-5

Cited by 25 publications

(14 citation statements)

References 14 publications

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“…While this appears plausible, the reaction conditions are very mild (120˚C reflux) compared to those published in the literature (for example, in the presence of a catalytic amount of azobisisobutyronitrile (AIBN) or UV irradiation in toluene). 10,11 On that basis, we believe that this pathway, though plausible, is not a possibility.…”

mentioning

confidence: 87%

Reactions of bis(tetrazole)phenylenes. Surprising formation of vinyl compounds from alkyl halides

Fleming¹,

Kelleher²,

Mahon

et al. 2005

Tetrahedron

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mentioning

confidence: 87%

Reactions of bis(tetrazole)phenylenes. Surprising formation of vinyl compounds from alkyl halides

Fleming¹,

Kelleher²,

Mahon

et al. 2005

Tetrahedron

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“…Furthermore, allyltin reagents are very important in organic and asymmetric synthesis, 2 as shown, for instance, The 119 Sn NMR spectra of the crude products resulting from these additions clearly showed that mixtures of at least three dienyltin adducts were obtained. In previous studies with monoand disubstituted alkynes, 6 we demonstrated that it was possible to improve the selectivity of this reaction using organotin hydrides with bulky organic ligands. In view of the poor regio-and stereoselectivity of the present hydrostannylation (Scheme 1), we considered the alternative addition of the more sterically demanding trineophyltin hydride 2 (neophyl -Neph-is 2-methyl-2-phenylpropyl) to enyne 1 under similar reaction conditions.…”

Section: Introductionmentioning

confidence: 88%

Bicyclic allyltin derivatives through selective “one pot” hydrostannation - Diels-Alder reaction

Ocampo¹,

Mandolesi²,

Koll³

2011

Arkivoc

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in recognition of their achievements in organic chemistry and their contributions in the development of the field in our country AbstractIn this paper we report a simple "one pot" procedure to functionalized allyltin derivatives from 1-ethynylcyclohexene. Radical addition of trineophyltin hydride gives quantitatively to (Z,E)-1-(2-trineophylstannylvinyl)cyclohexene, a conjugated dienyl-stannane that, via a [4+2] cycloaddition reaction (Diels-Alder) with activated dienophiles, affords substituted bicyclic unsaturated products with specific stereochemistry and a trialkylstannyl group in allylic position. The Stille reaction of the allyltin compound enables the synthesis of aryl substituted bicyclic compounds in moderate to good yields (48-85%).

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“…Replacement of the chlorine atom of the enyne with an alkyl group, 86 gives the same trend with Z-enyne substrates high selectivity and E-enynes producing mixtures of products. 87 Remarkably, this regiocontrol has been successfully extended to a wide range of enynes, 57,86,87 including those having a tri-or tetrasubstituted double bond. These results clearly suggest that the regioselectivity of H-Sn bond addition to enynes is controlled by the geometry of the double bond, the so-called Z-directing effect (ZDE) rather than the electronic, steric, or chelating properties of the substituents 87 (Scheme 44).…”

Section: Scheme 41mentioning

confidence: 94%

“…This problem has been addressed by the use of the more hindered trineophyltin hydride, which circumvents many of the protodestannylation and isomerization problems that plague reactions with tributyl-and trimethyltin analogues (Scheme 47). 57,96 Scheme 47. Pd-catalyzed hydrostannation of alkynyl ketones.…”

Section: Alkynes With Electron-withdrawing Substituentsmentioning

confidence: 99%

Hydrostannation of Alkynes

2019

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In this review, we present an overview of hydrostannation of alkynes until the end of 2018. Mechanism of the tin hydride addition on a triple bond is discussed at the beginning of this review in the presence of metal catalysts as Pd, Ru-based complexes, Lewis acids and under radical conditions. Then, stereoselectivity as well as regioselectivity aspects of tin hydride addition on the carbon triple bond is discussed using metal-catalysis, radical conditions or Lewis acids. In each of these items, the reactions will be studied for terminal alkynes and then, for internal alkynes. Applications of hydrostannation of alkynes using metal-catalysis is presented in a variety of total syntheses with Pd, Mo, Rh and Ru-complexes to provide highly functionalized vinyl stannanes derivatives as key-intermediates. Comparison with other methods providing vinyl stannanes using metallostannation followed by protonation is presented before the last section dealing with a summary of classical experimental conditions used to achieve the hydrostannation of alkynes.

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Stereoselective hydrostannation of substituted alkynes with trineophyltin hydride

Cited by 25 publications

References 14 publications

Reactions of bis(tetrazole)phenylenes. Surprising formation of vinyl compounds from alkyl halides

Reactions of bis(tetrazole)phenylenes. Surprising formation of vinyl compounds from alkyl halides

Bicyclic allyltin derivatives through selective “one pot” hydrostannation - Diels-Alder reaction

Hydrostannation of Alkynes

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