The asymmetric Heck reaction

Shibasaki, Masakatsu; Boden, Christopher D. J.; Kojima, Akihiko

doi:10.1016/s0040-4020(97)00437-7

Cited by 267 publications

(74 citation statements)

References 85 publications

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“…Almost at the same time, Shibasaki et al [60] reviewed a similar topic particularly aiming at the asymmetric Heck reaction. Since a variety of carbocyclic, heterocyclic and spirocyclic systems can be constructed, the asymmetric Heck reaction becomes a powerful method for the synthesis of both tertiary and quaternary chiral carbon centres, with an enantiomeric excess often in the range of 80% to 99%.…”

Section: Selectivitymentioning

confidence: 99%

Heck Reaction—State of the Art

Jagtap¹

2017

Catalysts

175

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Abstract:The Heck reaction is one of the most studied coupling reactions and is recognized with the Nobel Prize in Chemistry. Thousands of articles, hundreds of reviews and a number of books have been published on this topic. All reviews are written exhaustively describing the various aspects of Heck reaction and refer to the work done hitherto. Looking at the quantum of the monographs published, and the reviews based on them, we found a necessity to summarize all reviews on Heck reaction about catalysts, ligands, suggested mechanisms, conditions, methodologies and the compounds formed via Heck reaction in one review and generate a resource of information. One can find almost all the catalysts used so far for Heck reaction in this review.

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Section: Selectivitymentioning

confidence: 99%

Heck Reaction—State of the Art

Jagtap¹

2017

Catalysts

175

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“…Perhaps the most significant progress to date is the development of an enantioselective variant. [5] est, the great potential of the asymmetric variants of the intramolecular Heck reaction was demonstrated, leading to later success in this field. The majority of the reported examples involve intramolecular reactions, which allow for relatively easy control of alkene regiochemistry and geometry of the product and tolerate less reactive alkene substrates.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Heck Reaction

2004

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The asymmetric Heck reaction is a powerful method for the synthesis of both tertiary and quaternary chiral carbon centers, with an enantiomeric excess often greater than 80%, and in some cases much higher (up to 99% ee). A variety of carbocyclic and heterocyclic systems can be constructed, including spirocyclic systems. The scope of the reaction with respect to the product alkene isomerization is somewhat limited by problems of regioselectivity, however, these problems are surmountable, and a new generation of ligands that dissociate more rapidly from the products, might improve both enantio-and regiocontrol. A variety of chiral compounds prepared 5.2 N,N Ligands 5.3 P,P Ligands and Derivatives 5.4 Other Types of Ligands and Diastereoselective Reactions 6 Methodological Developments 7 Summary and Conclusions

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“…17,18 Steric or electronic effects in the formation of a C-C double bond strongly affect the direction of β-hydride elimination to produce distal products with high selectivities. Chirik 19 and Watson 20 very recently reported distal-selective C-C double-bond formations with nonbiased olefins achieved by elegant ligand choice in silyl Heck reactions.…”

Section: Synpacts Syn Lettmentioning

confidence: 99%

Challenges in the Substitution of Terminal C–C Double Bonds with Tertiary Alkyl groups

Nishikata

Ishikawa

2015

Synlett

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There are a few reports on the reaction of tertiary alkyl halide and alkene to produce an alkyl-substituted alkene. To establish tertiary alkylation of a C-C double bond, radical reaction is found to be one of the most promising protocols. In this paper, we highlight tertiary alkyl substitutions on C-C double bonds via atom-transfer radical substitution (ATRS) catalyzed by a copper salt and introduce the corresponding M-H reactions. 1Alkylation via the Mizoroki-Heck Reaction 2Tertiary Alkylative M-H-Type Reaction 3Regioselective Double-Bond Formation 4Summary and Perspectives

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The asymmetric Heck reaction

Cited by 267 publications

References 85 publications

Heck Reaction—State of the Art

Heck Reaction—State of the Art

Asymmetric Heck Reaction

Challenges in the Substitution of Terminal C–C Double Bonds with Tertiary Alkyl groups

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