Enantioselective Cyclization of Alkene Radical Cations.

Crich, David; Shirai, Michio; Rumthao, Sochanchingwung

doi:10.1002/chin.200405029

Cited by 2 publications

(2 citation statements)

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“…In order to determine the site-selectivity of the reaction, the ketone product was converted into a fluorescently labeled amine. 58 Clearly, either Pd(0) or Pd(II) can be confined nicely on the array.…”

Section: An Array-based Synthetic Strategymentioning

confidence: 99%

Using Physical Organic Chemistry To Shape the Course of Electrochemical Reactions

2018

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While organic electrochemistry can look quite different to a chemist not familiar with the technique, the reactions are at their core organic reactions. As such, they are developed and optimized using the same physical organic chemistry principles employed during the development of any other organic reaction. Certainly, the electron transfer that triggers the reactions can require a consideration of new "wrinkles" to those principles, but those considerations are typically minimal relative to the more traditional approaches needed to manipulate the pathways available to the reactive intermediates formed downstream of that electron transfer. In this review, three very different synthetic challenges-the generation and trapping of radical cations, the development of site-selective reactions on microelectrode arrays, and the optimization of current in a paired electrolysis-are used to illustrate this point.

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Section: An Array-based Synthetic Strategymentioning

confidence: 99%

Using Physical Organic Chemistry To Shape the Course of Electrochemical Reactions

2018

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“…They developed a stereoselective cyclization process for the synthesis of functionalized pyrrolidines 537 from βnitrophosphate radical cation precursors 536 by treatment with Bu 3 SnH and AIBN in benzene at reflux. 314 An interesting approach to synthesize substituted fivemembered ring nitrogen heterocycles has been described by Ojima and co-workers in 2002, who reported a rhodiumcatalyzed carbonylative silylcarbocyclization reaction of enynes. 315 The reaction was carried out in the presence of Rh 4 (CO) 12 as a catalyst, Me 2 PhSiH, and P(OEt) 3 at 105 °C and 20 atm of CO and led to the formation of the desired pyrrolidine 539 in 86% yield.…”

Section: Synthesis Of Pyrrolidines From Propargylaminesmentioning

confidence: 99%

Synthesis and Reactivity of Propargylamines in Organic Chemistry

et al. 2017

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Propargylamines are a versatile class of compounds which find broad application in many fields of chemistry. This review aims to describe the different strategies developed so far for the synthesis of propargylamines and their derivatives as well as to highlight their reactivity and use as building blocks in the synthesis of chemically relevant organic compounds. In the first part of the review, the different synthetic approaches to synthesize propargylamines, such as A couplings and C-H functionalization of alkynes, have been described and organized on the basis of the catalysts employed in the syntheses. Both racemic and enantioselective approaches have been reported. In the second part, an overview of the transformations of propargylamines into heterocyclic compounds such as pyrroles, pyridines, thiazoles, and oxazoles, as well as other relevant organic derivatives, is presented.

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Enantioselective Cyclization of Alkene Radical Cations.

Cited by 2 publications

References 1 publication

Using Physical Organic Chemistry To Shape the Course of Electrochemical Reactions

Using Physical Organic Chemistry To Shape the Course of Electrochemical Reactions

Synthesis and Reactivity of Propargylamines in Organic Chemistry

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