Organocatalytic Asymmetric Epoxidation and Aziridination of Olefins and Their Synthetic Applications

Zhu, Yingguang; Wang, Qian; Cornwall, Richard G.; Shi, Yian

doi:10.1021/cr500064w

Cited by 426 publications

(138 citation statements)

References 584 publications

(490 reference statements)

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“…Ozonolysis of known enoate 9 , 21 followed by nucleophilic addition of isopropenyl magnesium bromide and a tandem vinylation–Claisen process 22 afforded aldehyde 10 . Olefination of 10 23 and subsequent asymmetric Shi epoxidation 24 and TBAF desilylation rapidly provides cascade precursor 5 in six steps from enoate 9 . 25 …”

Section: Resultsmentioning

confidence: 99%

Rhodium-Catalyzed Endo-Selective Epoxide-Opening Cascades: Formal Synthesis of (−)-Brevisin

2015

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[Rh(CO)2Cl]2 is as an effective catalyst for endo-selective cyclizations and cascades of epoxy-(E)-enoate alcohols, thus enabling the synthesis of oxepanes and oxepane-containing polyethers from di- and trisubstituted epoxides. Syntheses of the ABC and EF ring systems of (−)-brevisin via all endo-diepoxide-opening cascades using this method constitute a formal total synthesis and demonstrate the utility of this methodology in the context of the synthesis of marine ladder polyether natural products.

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Section: Resultsmentioning

confidence: 99%

Rhodium-Catalyzed Endo-Selective Epoxide-Opening Cascades: Formal Synthesis of (−)-Brevisin

2015

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“…For details on this topic, it is advised to refer to a well-reviewed paper by Shi et al in 2014. 240 …”

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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“…In particular, the organocatalyzed asymmetric epoxidation of olefins is an important part of this field, and a number of these processes have been successfully applied to the total synthesis of various important molecules in the last 15 years. Actually, this topic was reviewed in 2014 by Shi et al [88], consequently only some representative examples will be detailed in this Section. The readers are invited to consult this comprehensive coverage for a complete coverage of the field.…”

Section: Asymmetric Organocatalyzed Epoxidations As Key Stepsmentioning

confidence: 99%

Applications of Chiral Three-membered Rings for Total Synthesis: A Review

Dalpozzo¹,

Lattanzi

Pellissier

2017

COC

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This review updates recent applications of asymmetric aziridination, azirination, thiirination, epoxidation, and cyclopropanation in the total synthesis of biologically active compounds, including natural products, using chiral substrates or chiral catalysts, covering the literature since 2000. The interest towards these synthetic methodologies of chiral three-membered rings has increased in the last decade, dictated either by the biological activities that display many naturally occurring products bearing a three-membered unit or by the ring strain of three-membered rings making them useful precursors of many more complex interesting molecules. Classic as well as modern protocols in asymmetric aziridinations, azirinations, epoxidations, thiirinations, and cyclopropanations have been widely applied as key steps of a number of syntheses of important products. Although the use of chiral substrates and auxiliaries is still highly employed particularly in asymmetric aziridination and cyclopropanation, the development of enantioselective catalytic methodologies has witnessed exponential growth during the last decade. The present review is subdivided into three parts, dealing successively with the use of chiral nitrogen-containing three-membered rings, chiral epoxides and thiiranes, and chiral cyclopropanes in total synthesis.

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Organocatalytic Asymmetric Epoxidation and Aziridination of Olefins and Their Synthetic Applications

Cited by 426 publications

References 584 publications

Rhodium-Catalyzed Endo-Selective Epoxide-Opening Cascades: Formal Synthesis of (−)-Brevisin

Rhodium-Catalyzed Endo-Selective Epoxide-Opening Cascades: Formal Synthesis of (−)-Brevisin

Chalcone: A Privileged Structure in Medicinal Chemistry

Applications of Chiral Three-membered Rings for Total Synthesis: A Review

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