Asymmetric Catalysis: Resin‐Bound Hydroxyprolylthreonine Derivatives in Enamine‐Mediated Reactions

Carpenter, Richard D.; Fettinger, James C.; Lam, Kit S.; Kurth, Mark J.

doi:10.1002/anie.200801811

Cited by 53 publications

(13 citation statements)

References 51 publications

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“…Carpenter et al [138] described organocatalytic chromanone synthesis under microwave irradiation. They have used resin bound dipeptide C80 as the catalyst.…”

Section: Organocatalytic Reactions Under Micro-wave Irradiationmentioning

confidence: 99%

Organocatalytic Reactions Under Unusual Conditions

Tomá¹,

Šebesta²,

Mečiarová

2011

COC

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Organocatalyzed reactions can often be advantageously performed in non-traditional reaction media. Use of ionic liquids, water or brine often leads to improved yields and selectivities of organocatalytic transformations. In terms of energy source, organocatalyzed reactions can be significantly accelerated by microwave irradiation, ultrasound or high pressure. Reactions without solvent and performed in ball mills are also reviewed.

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“…Carpenter et al [138] described organocatalytic chromanone synthesis under microwave irradiation. They have used resin bound dipeptide C80 as the catalyst.…”

Section: Organocatalytic Reactions Under Micro-wave Irradiationmentioning

confidence: 99%

Organocatalytic Reactions Under Unusual Conditions

Tomá¹,

Šebesta²,

Mečiarová

2011

COC

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“…The plausible reaction pathway, reported below for the asymmetric tandem oxa-Michael/aldol condensation (Scheme 47), An analogous mechanism should be followed when the procedure was performed with a supported catalyst such as 312. Indeed chromanone derivatives were constructed, by Kurth's group [87], with excellent stereoselectivity (up to 99% ee) by a TentaGel-bound (TG-bound) hydroxyprolylthreonine catalyst through a tandem aldol/Michael reaction between acetophenone and cycloalkanone derivatives assisted by microwave (Scheme 48). Results of the syntheses were chromanones with the 2-and 3-methyl groups being respectively trans and cis to the final ether.…”

Section: Cascade Reactionsmentioning

confidence: 99%

An Organocatalytic Approach to the Synthesis of Six-Membered Heterocycles

Gasperi¹,

Punzi²,

Migliorini³

et al. 2011

COC

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"""In the last few years, the new era of organocatalysis opened up an effective and efficient way to high yielding metal free, enantio- and diastereoselective reactions leading to six-membered heterocycles. This review provides an overview of the current achievements in the organocatalytic synthesis of these crucial building blocks. Ranging from hetero-Diels-Alder to cycloadditions, from one step cyclizations to cascade reactions, recent results offer new powerful tools to obtain six membered heterocycles with facile procedures in high yields and stereoselection, often leading to many new stereogenic centres in a single reaction. The total syntheses of natural products having heterocyclic ring formation as crucial stage, are also reported. When available, alternative supported organocatalysts have been examined""

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“…In an outstanding work, Kurth and coworkers controled the stereochemistry in the synthesis of optically active spirochromanones (Scheme 3.16) [49]. To do so, they first screened a library of TentaGel-supported peptides 41a-f, focusing their attention on two quasienantiomer di-tert-butoxy-protected hydroxyprolyl-threonine catalysts 41e-f.…”

Section: Polymer Supported Proline-peptidesmentioning

confidence: 99%