A Boron‐Based Synthesis of the Natural Product (+)‐<i>trans</i>‐Dihydrolycoricidine

Poe, Sarah L.; Morken, James P.

doi:10.1002/ange.201007135

Cited by 15 publications

(1 citation statement)

References 30 publications

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“…In conclusion, we have described a highly stereospecific Pd‐catalyzed decarboxylative arylation of 2,5‐cyclohexadiene‐1‐carboxylic acids. The resulting 5‐arylated‐1,3‐cyclohexadienes are useful bulding blocks in synthesis 14. The starting carboxylic acids are readily prepared by Birch reduction.…”

Section: Decarboxylative Coupling Of 1 a With Iodobenzene To Give 2 Amentioning

confidence: 99%

Intrinsic Green Phosphor Containing a {Y₅O₂₂} Pentamer Unit and a Carbonate Ligand Generated In Situ from Squaric Acid

Huang

Lai

Wang

2012

Chemistry A European J

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An unexpected green phosphor! The promising activator‐free yttrium metal–organic framework (MOF) [Y5(OH)6(HCO2)3(CO3)2‐(C4O4)] ⋅2.5 H2O consists of unique {Y5O22} pentamers and four types of ligands, the carbonate group of which was unprecedentedly in situ generated from squaric acid. This pure yttrium–MOF compound displays intrinsic green light and has proven to be the first hybrid‐yttrium‐host lattice to achieve near‐white‐light solely through Eu3+ doping (see figure).

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Section: Decarboxylative Coupling Of 1 a With Iodobenzene To Give 2 Amentioning

confidence: 99%

Intrinsic Green Phosphor Containing a {Y₅O₂₂} Pentamer Unit and a Carbonate Ligand Generated In Situ from Squaric Acid

Huang

Lai

Wang

2012

Chemistry A European J

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Synthesis of (+)‐trans‐Dihydrolycoricidine by an Organocatalytic Enantioselective Friedel–Crafts Reaction

et al. 2016

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The amaryllidaceae alkaloid (+ +)-trans-dihydrolycoricidine (1)w as synthesized by asymmetric organocatalytic Friedel-Craftsr eaction of sesamol with nitro-olefin followed by an intramolecular Henry reaction for constructiono ft he Cr ing system.C onstructiono ft he Br ing was achieved by am icrowave-assisted palladium-catalyzed CO insertion reaction. Finally,r egio-and stereoselective introductiono ft he third hydroxyl group (at C3) on the Cr ing afforded 1.

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Palladium‐Catalyzed Synthesis and Isolation of Functionalized Allylboronic Acids: Selective, Direct Allylboration of Ketones

2012

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Allyl boronates are very important reagents in advanced organic synthesis for the allylation of carbonyl compounds [1] and in cross-coupling [2] reactions. A practically unrivalled property of allylboronates is their highly regio-and stereoselective addition to carbonyl compounds to afford homoallylic alcohols. [1a-d, 3] This high selectivity is mainly based on two factors: 1) Allylboronates are configurationally stable, and unlike many allyl metal compounds [4] (such as allylGrignard reagents, allyl lithium compounds or allylboranes) do not undergo metallotropic rearrangement and E/Z isomerization at ambient conditions. 2) The six-membered ring transition state (TS) of the allylboration of carbonyl compounds is highly conformationally constrained, which leads to a strong differentiation in the stereoselection process. [3a, 5] Method development for broadening the number of accessible functionalized allyl boronates is one of the most important challenges in organoboron chemistry.In allylboration reactions with allylboronic esters, allyl pinacolborate (allyl-Bpin) reagents are most frequently applied as the allyl source, [1a-d] as allyl-Bpins can be easily handled and the functionalized derivatives can be obtained by metal-catalyzed borylation of the allyl precursors with bis(pinacolato)diboron (B 2 pin 2 ) as the boronate source. [6] Problems in synthetic applications arise from the relatively low reactivity of allyl-Bpin compounds towards most carbonyl compounds. Although aldehydes easily react with allyl-Bpin without catalysts, ketones do not. There are very few attempts at the direct allylation of ketones by functionalized allylBpins or their ester analogues reported in the literature.

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A Boron‐Based Synthesis of the Natural Product (+)‐trans‐Dihydrolycoricidine

Cited by 15 publications

References 30 publications

Intrinsic Green Phosphor Containing a {Y₅O₂₂} Pentamer Unit and a Carbonate Ligand Generated In Situ from Squaric Acid

Intrinsic Green Phosphor Containing a {Y₅O₂₂} Pentamer Unit and a Carbonate Ligand Generated In Situ from Squaric Acid

Synthesis of (+)‐trans‐Dihydrolycoricidine by an Organocatalytic Enantioselective Friedel–Crafts Reaction

Palladium‐Catalyzed Synthesis and Isolation of Functionalized Allylboronic Acids: Selective, Direct Allylboration of Ketones

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A Boron‐Based Synthesis of the Natural Product (+)‐trans‐Dihydrolycoricidine

Cited by 15 publications

References 30 publications

Intrinsic Green Phosphor Containing a {Y5O22} Pentamer Unit and a Carbonate Ligand Generated In Situ from Squaric Acid

Intrinsic Green Phosphor Containing a {Y5O22} Pentamer Unit and a Carbonate Ligand Generated In Situ from Squaric Acid

Synthesis of (+)‐trans‐Dihydrolycoricidine by an Organocatalytic Enantioselective Friedel–Crafts Reaction

Palladium‐Catalyzed Synthesis and Isolation of Functionalized Allylboronic Acids: Selective, Direct Allylboration of Ketones

Contact Info

Product

Resources

About

Intrinsic Green Phosphor Containing a {Y₅O₂₂} Pentamer Unit and a Carbonate Ligand Generated In Situ from Squaric Acid

Intrinsic Green Phosphor Containing a {Y₅O₂₂} Pentamer Unit and a Carbonate Ligand Generated In Situ from Squaric Acid