Direct organocatalytic in situ generation of novel push–pull dienamines: application in tandem Claisen–Schmidt/iso-aromatization reactions

Ramachary, Dhevalapally B.; Ramakumar, Kinthada; Kishor, Mamillapalli

doi:10.1016/j.tetlet.2005.08.051

Cited by 47 publications

(16 citation statements)

References 33 publications

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“…[5,6] Among these important structures, the amino acid proline [7] and the MacMillan's imidazolidinones [8] have become one of the most efficient organocatalysts. However, in the last years, diarylprolinol derivatives have appeared as a capable class of organocatalysts, [9] showing a remarkable generality compared with proline and imidazolidinones, which have displayed its efficiency in a great number of processes firstly focused on the α-, [10] β-, [11] and γ-functionalization [12] of carbonyl compounds, involving enamine, iminium-ion and dienamine activation or a combination of them. [13] Moreover, these catalysts have been also applied in diastereo-and enantioselective domino, one-pot, and multicomponent reactions.…”

Section: Introductionmentioning

confidence: 99%

Diarylprolinol Derivatives in Organocatalysis From Another Point of View: Structural Aspects

Marqués‐López¹,

Herrera²

2011

COC

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The synthesis of complex active molecules has afforded the search for new methods and new processes in organic synthesis. In this context, organic metal free catalysis has appeared as a powerful tool being complementary to metal catalysis in the field of asymmetric synthesis. The success of this methodology has been increasing in the last decade and the research for new organocatalytic systems as well as new applications has attracted the interest of many research groups. Among all organocatalysts, diarylprolinol derivatives have emerged as powerful scaffolds for asymmetric catalysis, proof of that is the huge number of publications reported using this kind of structure as catalysts. However, only in a few cases, different aspects of the catalysts structures and additional additives have been largely studied and a plausible explanation has been given. In this sense, this review treats to illustrate these important and scarce examples and to give a very general vision relating to the application of diarylprolinol derivatives in organocatalytic transformations from another point of view: structural aspects. The influence of catalyst structure, electronic effects, and the use of additives will be the aim of discussion and comment in this work.

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Section: Introductionmentioning

confidence: 99%

Diarylprolinol Derivatives in Organocatalysis From Another Point of View: Structural Aspects

Marqués‐López¹,

Herrera²

2011

COC

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“…Claisen-Schmidt/iso-aromatization (CS/IA) cascade reaction to furnish the functionalized phenols based on the push-pull dienamine (PPD) chemistry (Scheme 20). 28 In 2005, we developed a new, regioselective, one-step, cascade CS/IA reaction of an aldehyde 1 possessing a non-enolizable carbonyl function with highly substituted Hagemann's esters 45 under diamine 5c catalysis to furnish highly substituted phenols 46 in good yields. The yields and regioselectivities were good.…”

Section: Rapid Synthesis Of Functionalized Phenols Based On Push-pull...mentioning

confidence: 99%

“…Evidence for a pathway involving in situ formation of novel push-pull dienamines from 45 and 5c was presented along with examples demonstrating the amenability of the process to combinatorial chemistry (Scheme 20). 28 This experimentally simple and environmentally friendly approach can be used to construct highly substituted phenols 46 in a regiospecific fashion. For the first time in organocatalysis, push-pull dienamines were generated in situ and shown to be a very good platform for cascade reactions.…”

Section: Rapid Synthesis Of Functionalized Phenols Based On Push-pull...mentioning

confidence: 99%

Sequential one-pot combination of multi-component and multi-catalysis cascade reactions: an emerging technology in organic synthesis

2011

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Creating sequential one-pot combinations of multi-component reactions (MCRs) and multi-catalysis cascade (MCC) reactions is a challenging task that has already emerged as a new technology in synthetic organic chemistry. Through one-pot sequential combination of MCRs/MCC reactions, the chemical products (fine chemicals, agrochemicals and pharmaceuticals) that add value to our lives can be produced with less waste and greater economic benefits. Within this Emerging Area, we describe our recent developments and designs for sequential one-pot MCRs/MCC reactions to facilitate their realization as biomimetics in organic chemistry.

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“… Ramachary's approach to the synthesis of the functionalized phenols 123 based on the push‐pull dienamine platform 28a,28b…”

Section: Ramachary Dienamines (Push‐pull Dienamines) – In Situ Genmentioning

confidence: 99%

Dienamine Catalysis: An Emerging Technology in Organic Synthesis

2011

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High-yielding asymmetric synthesis of bioactive molecules with the aid of mild catalysis is an efficient approach in reaction engineering. In the early days, synthetic chemists mainly focused on the synthesis of complex molecules, but not much on reaction efficiency and eco-friendly conditions. Recent investigations have been directed towards the development of atom economy and of eco-friendly and enantioselective syn-

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Direct organocatalytic in situ generation of novel push–pull dienamines: application in tandem Claisen–Schmidt/iso-aromatization reactions

Cited by 47 publications

References 33 publications

Diarylprolinol Derivatives in Organocatalysis From Another Point of View: Structural Aspects

Diarylprolinol Derivatives in Organocatalysis From Another Point of View: Structural Aspects

Sequential one-pot combination of multi-component and multi-catalysis cascade reactions: an emerging technology in organic synthesis

Dienamine Catalysis: An Emerging Technology in Organic Synthesis

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