Ammonium Ylides as Building Blocks for Alkaloid Synthesis

Bur, Scott K.; Padwa, Albert

doi:10.1002/9781118342886.ch13

Cited by 4 publications

(1 citation statement)

References 154 publications

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“…Rearrangements of ammonium ylides like the [1,2]-Stevens or the [2,3]-Sommelet-Hauser rearrangement are classical textbook examples in organic chemistry. [3][4][5][6][7][8][9] In contrast to the situation in phosphonium or arsonium ylides, the energetically higher lying σ*-orbitals of the C-N bonds in ammonium ylides provide only little stabilization for the negative charge adjacent to the onium center. 10 Therefore, ammonium ylides have a propensity to undergo rearrangements to achieve a thermodynamic stabilization of the unfavorable ylide state while the analogues of the higher pnictogens are known for intermolecular reactions like olefinations (e.g., the Wittig reaction) or epoxide formations.…”

Section: Introductionmentioning

confidence: 99%

Rearrangements of Nitrile-Stabilized Ammonium Ylides

Lahm¹,

Pacheco²,

Opatz³

2014

Synthesis

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Rearrangements of nitrile-stabilized ammonium ylides are useful reactions for the construction of alkylamines, nitrogen heterocycles, or carbonyl compounds. In spite of their attractive synthetic potential, they are much less frequently used than rearrangements of ammonium ylides either carrying charge-stabilizing carbonyl groups or being devoid of additional stabilization of the negative charge. This review focuses on different classes of rearrangements of nitrile-stabilized ammonium ylides as well as their application in synthetic organic chemistry.

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Section: Introductionmentioning

confidence: 99%

Rearrangements of Nitrile-Stabilized Ammonium Ylides

Lahm¹,

Pacheco²,

Opatz³

2014

Synthesis

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Ammonium Ylide Mediated Cyclization Reactions

2018

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The use of readily accessible ammonium ylides for (asymmetric) transformations, especially cyclization reactions, has received considerable attention over the past two decades. A variety of highly enantioselective protocols to facilitate annulation reactions have recently been introduced as an alternative to other common methods including S-ylide-mediated strategies. It is the intention of this short review to provide an introduction to this field by highlighting the potential of ammonium ylides for (asymmetric) cyclization reactions as well as to present the limitations and challenges of these methods.

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