Enantioselective Synthesis of α-Stereogenic γ-Keto Esters via Formal Umpolung

Prakash, G. K. Surya; Wang, Fang; Zhang, Zhe; Ni, Chuanfa; Haiges, Ralf; Oláh, George A.

doi:10.1021/ol301112m

Cited by 33 publications

(13 citation statements)

References 71 publications

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“…188,191 The addition of malononitrile to a chalcone derivative in the presence of a quinine-derived bifunctional thiourea tertiary amine ( 21 ) as a catalyst results in compound 15 . The mechanism of the Michael addition of malononitrile to chalcones has also been examined using theoretical calculations.…”

Section: Chemical Reactions Related To Michael Acceptorsmentioning

confidence: 99%

Chalcone: A Privileged Structure in Medicinal Chemistry

et al. 2017

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Privileged structures have been widely used as an effective template in medicinal chemistry for drug discovery. Chalcone is a common simple scaffold found in many naturally occurring compounds. Many chalcone derivatives have also been prepared due to their convenient synthesis. These natural products and synthetic compounds have shown numerous interesting biological activities with clinical potentials against various diseases. This review aims to highlight the recent evidence of chalcone as a privileged scaffold in medicinal chemistry. Multiple aspects of chalcone will be summarized herein, including the isolation of novel chalcone derivatives, the development of new synthetic methodologies, the evaluation of their biological properties, and the exploration of the mechanisms of action as well as target identification. This review is expected to be a comprehensive, authoritative, and critical review of the chalcone template to the chemistry community.

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Section: Chemical Reactions Related To Michael Acceptorsmentioning

confidence: 99%

Chalcone: A Privileged Structure in Medicinal Chemistry

et al. 2017

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“…The resulting g-keto esters are produced in moderate yields and high enantioselectivity (Scheme 62). [137] Enantioselective conjugate additions of nitromethane 124 to chromenes were reported by Wang et al achieving very good results. [138] Again a low diastereoselectivity is observed by deployment of other nitroalkanes (Scheme 63).…”

Section: Prakash Et Al Applied Nitro-(phenylsulfonyl)-methane 130mentioning

confidence: 99%

“…The alkylation is followed by an oxidative methanolysis via a two‐step one‐pot protocol. The resulting γ‐keto esters are produced in moderate yields and high enantioselectivity (Scheme ) 137…”

Section: Henry Reaction and Related Reactionsmentioning

confidence: 99%

Recent Advances in Organocatalytic Methods for Asymmetric CC Bond Formation

Scheffler

Mahrwald

2013

Chemistry A European J

200

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Beyond a doubt organocatalysis belongs to the most exciting and innovative chapters of organic chemistry today. Organocatalysis has emerged not only as a complement to metal-catalyzed reactions and to biocatalysis over the last decade, but also provides new asymmetric organocatalyzed reactions that cannot be accomplished by metal- or biocatalyzed reactions so far. A large number of organocatalytic processes are already well established in organic synthesis. Nevertheless, the number of publications in this field is still on the increase; new important results are produced constantly. This review gives a detailed overview of the latest developments and main streams in organocatalyzed asymmetric CC bond formation processes of the last three years. It is intended to outline the most important current findings focused on especially new synthetic methodologies.

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“…Seminal work by Hu and co‐workers showed that α‐fluorodi(benzenesulfonyl)methane, (PhSO 2 ) 2 CFH, reacts with enones faster than di(benzenesulfonyl)methane, (PhSO 2 ) 2 CH 2 . Similarly, the urea‐catalyzed reactions between α‐fluoro‐α‐nitro(benzenesulfonyl)methane and chalcones are also more rapid than those of nitro(benzenesulfonyl)methane ,. Furthermore, despite that the nucleophilic addition of (PhSO 2 ) 2 CFLi to benzaldehyde leads to the corresponding alcohol in high yield, no adduct was obtained in the reaction with (PhSO 2 ) 2 CHLi or (PhSO 2 ) 2 CClLi under similar reaction conditions .…”

Section: Figurementioning

confidence: 99%

The Nucleophilicity of Persistent α‐Monofluoromethide Anions

et al. 2016

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a-Fluorocarbanions are key intermediates in nucleophilic fluoroalkylation reactions.A lthough frequently discussed, the origin of the fluorine effect on the reactivity of afluorinated CH acids has remained largely unexplored. We have nowinvestigated the kinetics of aseries of reactions of asubstituted carbanions with reference electrophiles to elucidate the effects of a-F, a-Cl, and a-OMe substituents on the nucleophilic reactivities of carbanions.

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Enantioselective Synthesis of α-Stereogenic γ-Keto Esters via Formal Umpolung

Cited by 33 publications

References 71 publications

Chalcone: A Privileged Structure in Medicinal Chemistry

Chalcone: A Privileged Structure in Medicinal Chemistry

Recent Advances in Organocatalytic Methods for Asymmetric CC Bond Formation

The Nucleophilicity of Persistent α‐Monofluoromethide Anions

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