Organocatalysis in Total Synthesis

Marqués‐López, Eugenia; Herrera, Raquel P.

doi:10.1002/9783527658862.ch44

Cited by 11 publications

(4 citation statements)

References 203 publications

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“…In the past decade, imine/enamine catalysis rapidly established a prominent position in the total synthesis of alkaloids with an accelerating trajectory in the number of applications. − Although early applications were aimed at the synthesis of simpler compounds, the sophistication of targets increased rapidly to include complex Vinca alkaloids and marine natural products such as diazonamide. Saturated or α,β-unsaturated aldehydes are used as reagents in almost all the reported examples.…”

Section: Asymmetric Catalysismentioning

confidence: 99%

Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

et al. 2016

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The main objective of this review is to provide a comprehensive survey of methods used for stereoselective construction of carbon-nitrogen bonds during the total synthesis of nitrogen-containing natural products that have appeared in the literature since 2000. The material is organized by specific reaction in order of decreasing number of applications in natural product synthesis. About 800 total syntheses of natural products with stereogenic carbon-nitrogen bonds described since 2000 have been reviewed.

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Section: Asymmetric Catalysismentioning

confidence: 99%

Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

et al. 2016

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“…The products can be obtained on a large scale in a straightforward fashion and high optical purity, as exemplified in the two cases. Efforts to employ this organocatalyzed process in the synthesis of natural products and bioactive analogues are currently in progress in our laboratories …”

Section: Discussionmentioning

confidence: 99%

Brønsted Acid-Catalyzed, Diastereo- and Enantioselective, Intramolecular Oxa-Diels–Alder Reaction of ortho-Quinone Methides and Unactivated Dienophiles

Ukis

Schneider

2019

J. Org. Chem.

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A stereoselective, phosphoric acid-catalyzed synthesis of dihydrochromenochromenes has been developed using transient ortho-quinone methides (o-QMs). Three contiguous stereogenic centers were formed with excellent yields, partially as single diastereomers and with moderate to excellent enantioselectivity. This intramolecular hetero-Diels− Alder reaction features unactivated dienophiles and o-QM precursors tethered by a simple phenoxy linker and furnishes cycloadducts with a prominent structural motif found in many natural products. Through an appropriate choice of dienophile configuration and backbone substitution either exo-or endo-stereoisomers were formed selectively with up to a 96:04 enantiomeric ratio.

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“…Asymmetric synthesis is among the areas that have experienced the fastest growth thanks to catalysis, − so much so that several remarkable privileged catalysts are well-established in the literature . Nowadays, not only asymmetric metallic and enzymatic catalysis but also organocatalysis, − the use of small organic molecules as catalysts, are totally established performing a wide number of novel enantioselective transformations. Many of these free-metal strategies have led to important and seminal contributions, even carrying out unknown transformations up to date expanding the repertoire of reactions.…”

Section: Introductionmentioning

confidence: 99%

Chiral Hypervalent Iodines: Active Players in Asymmetric Synthesis

2019

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Asymmetric organocatalytic oxidations have been witnessed to an impressive development in the last years thanks to the establishment of important chiral hypervalent iodines(III/V). Many different approaches involving both stoichiometric and catalytic versions have provided a fundamental advance in this area within asymmetric synthesis. The easily handing, nontoxic, mild, environmentally friendly (green oxidants), and high stability that are features of these reagents have been applied to many reactions and also have allowed exploring further unprecedented enantioselective transformations. The intention of the present review is thus to highlight as a whole the many approaches utilized up to date to prepare chiral iodines(III/V), as well as their reactivity in a comprehensive manner.

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Organocatalysis in Total Synthesis

Cited by 11 publications

References 203 publications

Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

Cutting-Edge and Time-Honored Strategies for Stereoselective Construction of C–N Bonds in Total Synthesis

Brønsted Acid-Catalyzed, Diastereo- and Enantioselective, Intramolecular Oxa-Diels–Alder Reaction of ortho-Quinone Methides and Unactivated Dienophiles

Chiral Hypervalent Iodines: Active Players in Asymmetric Synthesis

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