Synthesis of (Z)-Cinnamate Esters by Nickel-Catalyzed Stereoinvertive Deoxygenation of trans-3-Arylglycidates

Akkarasamiyo, Sunisa; Chitsomkhuan, Saranya; Buakaew, Supawadee; Samec, Joseph S. M.; Chuawong, Pitak; Kuntiyong, Punlop

doi:10.1055/s-0040-1719911

Cited by 5 publications

(3 citation statements)

References 28 publications

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“…All the reactions were run in duplicate. The spectra of all the products obtained were in agreement with the data reported in the literature (see Supplementary Materials ) [ 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 ].…”

Section: Methodssupporting

confidence: 88%

Highly Z-Selective Horner–Wadsworth–Emmons Olefination Using Modified Still–Gennari-Type Reagents

Janicki

Kiełbasiński

2022

Molecules

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In this report, new, easily accessible reagents for highly Z-selective HWE reactions are presented. Alkyl di-(1,1,1,3,3,3-hexafluoroisopropyl)phosphonoacetates, structurally similar to Still–Gennari type reagents, were tested in HWE reactions with a series of various aldehydes. Very good Z-selectivity (up to a 98:2 Z:E ratio) was achieved in most cases along with high yields. Application of the new reagents may be a valuable, practical alternative to the well-established Still–Gennari or Ando Z-selective carbonyl group olefination protocols.

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Section: Methodssupporting

confidence: 88%

Highly Z-Selective Horner–Wadsworth–Emmons Olefination Using Modified Still–Gennari-Type Reagents

Janicki

Kiełbasiński

2022

Molecules

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“…Stereoinvertive deoxygenation of trans ‐stilbene oxides to cis ‐stilbenes have been reported by Li and co‐workers using copper nano cube with [Si−B] and LiHMDS (Scheme 1B‐c) [12i] . Recently, we reported the stereoinvertive deoxygenation of trans ‐3‐arylglycidates to ( Z )‐cinnamate esters using a simple catalytic system comprising nickel triflate and triphenylphosphine (Scheme 1B‐d) [12j] . In this work, we investigated and expanded scope of the stereoinvertive deoxygenation of epoxides using a catalytic system based on Ni/PPh 3 as well as a mechanistic study to get a better understanding on the scope and limitation of this reaction.…”

Section: Introductionmentioning

confidence: 82%

Nickel‐Catalyzed Stereospecific Deoxygenation of trans‐ Aromatic Epoxides to (Z)‐Alkenes: An Efficient Route to Access (Z)‐Cinnamic Acid Derivatives

Akkarasamiyo,

Chitsomkhuan,

Buakaew

et al. 2024

Asian J Org Chem

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A stereospecific deoxygenation of trans‐epoxy cinnamic acid derivatives to access (Z)‐cinnamamides, (Z)cinnamyl alcohol and (Z)‐cinnamyl amines using a catalytic system based on nickel triflate and triphenylphosphine has been developed. The desired products were obtained in good to excellent yield (up to 92% isolated yield) and excellent stereospecificity (Z:E ratio up to > 99:1). The transformation has a broad functional group tolerance including amides, amines, alcohols and esters. The power of the methodology was demonstrated in the key step of the total synthesis of biologically active natural product, N‐cis‐feruloyl tyramine from readily available ferulic acid. A reaction mechanism involving activation of epoxide via coordination of the oxygen atom and the neighboring O‐ or N‐atoms to the nickel catalyst and formation of Ph3P‐carbon bond is proposed. This method is important for synthesis of highly desirable functionalized (Z)‐alkenes from readily available (E)‐alkenes.

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“…Moreover, an efficient and selective approach to access tetrahydroindeno[1,2- a ]indenes was reported by Ploypradith 13 via a key acid-mediated transannular cyclization step between 1,3,5-trimethoxybenzene and benzannulated cyclooctenes containing tertiary alcohols. Akkarasamiyo 14 utilized nickel triflate in combination with triphenylphosphine to perform the stereoinvertive deoxygenation of trans -3-arylglycidates to prepare a panel of (Z) -cinnamate esters. The reaction showed broad functional group tolerance with high stereoselectivity.…”

Section: (1) Synthetic Methodologymentioning

confidence: 99%

Cluster Preface: Organic Chemistry in Thailand

Wacharasindhu¹

2022

Synlett

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This SYNLETT cluster highlights research work conducted in universities across Thailand. As a country rich in biodiversity, chemical research in Thailand was originally founded on the study of natural products. The discovery and development of novel, biologically active agents has contributed to drug discovery and advanced the development of novel compounds.1 Since the 1990s, the growth of petrochemical industries in Southeast Asia has spurred chemical research on synthetic methodologies, the creation of high-value compounds from petroleum-based starting materials and polymer sciences. The results have led to significant economic and strategic advantages that have enabled the competitiveness of local petrochemical industries. Moving into the new era, Thailand and the region faces global sustainability challenges. Green chemistry has also become a key theme for driving chemical research, which is expected to help in generating new ideas and innovations to deliver a more sustainable society. This cluster contains 27 articles that have been submitted from 12 different Thai universities. The articles are organized into 3 main themes, as outlined below.

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Synthesis of (Z)-Cinnamate Esters by Nickel-Catalyzed Stereoinvertive Deoxygenation of trans-3-Arylglycidates

Cited by 5 publications

References 28 publications

Highly Z-Selective Horner–Wadsworth–Emmons Olefination Using Modified Still–Gennari-Type Reagents

Highly Z-Selective Horner–Wadsworth–Emmons Olefination Using Modified Still–Gennari-Type Reagents

Nickel‐Catalyzed Stereospecific Deoxygenation of trans‐ Aromatic Epoxides to (Z)‐Alkenes: An Efficient Route to Access (Z)‐Cinnamic Acid Derivatives

Cluster Preface: Organic Chemistry in Thailand

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