Stereospecific diaza-Cope rearrangement as an efficient tool for the synthesis of DPEDA pyridine analogs and related C<sub>2</sub>-symmetric organocatalysts

Kucherenko, Alexander S.; Kostenko, Alexey A.; Gerasimchuk, Vasiliy V.; Zlotin, Sergei G.

doi:10.1039/c7ob01852e

Cited by 7 publications

(2 citation statements)

References 61 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…A similar situation is observed in asymmetric reactions over chiral organocatalysts. A typical example of such reactions is two-component reactions such as aldol reactions of acetone with α-ketoesters, reactions of cyclohexanone derivatives and β-nitrostyrenes (Michael reactions), nitroaldol (Henry) reactions [39,[142][143][144][145][146][147][148], etc. Two plausible transition states TS-R and TS-S ( Figure 13 Figure 14 shows two possible favoured and two disfavoured intermediates which are different from the viewpoint of an approach of the reagents to C2 33 (a front or rear approach).…”

Section: (C2)mentioning

confidence: 99%

Сhiral and Racemic Fields Concept for Understanding of the Homochirality Origin, Asymmetric Catalysis, Chiral Superstructure Formation from Achiral Molecules, and B-Z DNA Conformational Transition

2019

Self Cite

View full text Add to dashboard Cite

The four most important and well-studied phenomena of mirror symmetry breaking of molecules were analyzed for the first time in terms of available common features and regularities. Mirror symmetry breaking of the primary origin of biological homochirality requires the involvement of an external chiral inductor (environmental chirality). All reviewed mirror symmetry breaking phenomena were considered from that standpoint. A concept of chiral and racemic fields was highly helpful in this analysis. A chiral gravitational field in combination with a static magnetic field (Earth’s environmental conditions) may be regarded as a hypothetical long-term chiral inductor. Experimental evidences suggest a possible effect of the environmental chiral inductor as a chiral trigger on the mirror symmetry breaking effect. Also, this effect explains a conformational transition of the right-handed double DNA helix to the left-handed double DNA helix (B-Z DNA transition) as possible DNA damage.

show abstract

Section: (C2)mentioning

confidence: 99%

Сhiral and Racemic Fields Concept for Understanding of the Homochirality Origin, Asymmetric Catalysis, Chiral Superstructure Formation from Achiral Molecules, and B-Z DNA Conformational Transition

2019

Self Cite

View full text Add to dashboard Cite

show abstract

“…As aplicações recentes que ilustram rearranjos de Cope também foram descritos por outros pesquisadores. [93][94][95][96][97][98][99][100] Esquema 30. Proposta mecanistica para obtenção de de hapalindole e fischerindole Esquema 31.…”

Section: Aplicações Do Rearranjo De Cope Da Química Dos Produtos Natuunclassified

Recent Advancement of the Cope Rearrangement in Organic Synthesis

et al. 2019

View full text Add to dashboard Cite

The Cope rearrangement is a well-known reaction involving the [3,3]-sigmatropic rearrangement of 1,5-dienes. These rearrangements can be performed thermally or photochemically. This manuscript it is a literature review of major Cope rearrangements commonly used in organic synthesis over the past 18 years. Among the fundamental chemical transformations in organic synthesis, the [3,3]-sigmatropic rearrangement occupies a unique position as a powerful, reliable, and well-defined method for the stereoselective construction of carbon-carbon or carbon-heteroatom bonds. Cope rearrangement is among one the bestknown pericyclic reactions governed by the Woodward-Hoffmann rules. ResumoO Rearranjo de Cope é uma reação bem conhecida envolvendo o rearranjo [3,3]-sigmatrópico de 1,5-dienos. Esses rearranjos podem ser realizados termicamente ou fotoquimicamente. Este manuscrito trata-se de uma revisão bibliográfica sobre os rearranjos de Cope mais usados em síntese orgânica nos últimos 18 anos. Entre as transformações químicas fundamentais em síntese orgânica, o rearranjo [3,3]-sigmatrópico ocupa uma posição única como um método poderoso, confiável e bem definido para a construção estereosseletiva de ligações carbonocarbono ou carbono-heteroátomo. O rearranjo de Cope está entre uma das mais conhecidas reações pericíclicas usando a regra de Woodward-Hoffmann.

show abstract

Enantioselective Cross‐Aldol Reaction with Ketones and Non‐Enolizable Ketones Catalyzed by Tetrapeptides

et al. 2021

View full text Add to dashboard Cite

An efficient strategy shaping the construction of (R)-3-alkyl-3hydroxyindolin-2-one and (S)-5-trifluoromethyl-4-hydroxy-4-arylpentan-2-one derivatives catalyzed by the β-turn tetrapeptide catalyst under mild conditions was developed. Various isatins and ketones could participate in this reaction, and the desired adducts were obtained with excellent yield (up to 99 %) and moderate to high enantioselectivity (ee up to 85 %) and excellent diastereoselectivity (dr up to > 20 : 1). Moreover, a series of trifluoromethyl ketones with ketones also could participate in this reaction, and the resulting β-trifluoromethylβ-hydroxy ketones with excellent yields and moderate enantioselectivities (ee up to 58 %) were obtained. In addition, the strategy afforded better results than natural papain.

show abstract

Stereospecific diaza-Cope rearrangement as an efficient tool for the synthesis of DPEDA pyridine analogs and related C₂-symmetric organocatalysts

Cited by 7 publications

References 61 publications

Сhiral and Racemic Fields Concept for Understanding of the Homochirality Origin, Asymmetric Catalysis, Chiral Superstructure Formation from Achiral Molecules, and B-Z DNA Conformational Transition

Сhiral and Racemic Fields Concept for Understanding of the Homochirality Origin, Asymmetric Catalysis, Chiral Superstructure Formation from Achiral Molecules, and B-Z DNA Conformational Transition

Recent Advancement of the Cope Rearrangement in Organic Synthesis

Enantioselective Cross‐Aldol Reaction with Ketones and Non‐Enolizable Ketones Catalyzed by Tetrapeptides

Contact Info

Product

Resources

About

Stereospecific diaza-Cope rearrangement as an efficient tool for the synthesis of DPEDA pyridine analogs and related C2-symmetric organocatalysts

Cited by 7 publications

References 61 publications

Сhiral and Racemic Fields Concept for Understanding of the Homochirality Origin, Asymmetric Catalysis, Chiral Superstructure Formation from Achiral Molecules, and B-Z DNA Conformational Transition

Сhiral and Racemic Fields Concept for Understanding of the Homochirality Origin, Asymmetric Catalysis, Chiral Superstructure Formation from Achiral Molecules, and B-Z DNA Conformational Transition

Recent Advancement of the Cope Rearrangement in Organic Synthesis

Enantioselective Cross‐Aldol Reaction with Ketones and Non‐Enolizable Ketones Catalyzed by Tetrapeptides

Contact Info

Product

Resources

About

Stereospecific diaza-Cope rearrangement as an efficient tool for the synthesis of DPEDA pyridine analogs and related C₂-symmetric organocatalysts