Enantioselective Synthesis of Functionalized 4-Aryl Hydrocoumarins and 4-Aryl Hydroquinolin-2-ones via Intramolecular Vinylogous Rauhut-Currier Reaction of para-Quinone Methides.

@article{Zhang2017EnantioselectiveSO,
  title={Enantioselective Synthesis of Functionalized 4-Aryl Hydrocoumarins and 4-Aryl Hydroquinolin-2-ones via Intramolecular Vinylogous Rauhut-Currier Reaction of para-Quinone Methides.},
  author={Xiang‐Zhi Zhang and Kang-Ji Gan and Xiao-Xue Liu and Yuhua Deng and Fang-Xin Wang and Ke‐Yin Yu and Jing Zhang and Chun‐An Fan},
  journal={Organic letters},
  year={2017},
  volume={19 12},
  pages={
          3207-3210
        }
}
A novel strategy for the asymmetric construction of functionalized 4-aryl-3,4-dihydrocoumarins and 4-aryl-3,4-dihydroquinolin-2-ones via an intramolecular vinylogous Rauhut-Currier reaction of para-quinone methides (p-QMs) under the bifunctional catalysis of chiral amine-phosphine is described. This intramolecular mode for the catalytic enantioselective 1,6-conjugate addition of p-QMs has been explored for the first time, delivering two types of synthetically important heterocycles in high… 
76 Citations

Palladium-Catalyzed Asymmetric (2+3) Annulation of p-Quinone Methides with Trimethylenemethanes: Enantioselective Synthesis of Functionalized Chiral Spirocyclopentyl p-Dienones.

A novel asymmetric catalytic (2+3) annulation of p-quinone methides with CN-substituted trimethylenemethane is described under palladium catalysis, providing an alternative approach for the

Catalytic Asymmetric Hydrogenation of 3-Ethoxycarbonyl Quinolin-2-ones and Coumarins.

A protocol of iridium catalyzed asymmetric hydrogenation of 4-alkyl substituted 3-ethoxycarbonyl quinolin-2-ones and coumarins has been reported, providing a wide range of chiral

Phosphoric Acid Catalyzed Aldehyde Addition to in Situ Generated o-Quinone Methides: An Enantio- and Diastereoselective Entry toward cis-3,4-Diaryl Dihydrocoumarins.

A highly stereoselective, phosphoric acid catalyzed synthesis of cis-3,4-diarylchromanols through reaction of o-hydroxybenzhydryl alcohols and aryl acetaldehydes is reported, with good overall yields and very good diastereo- and enantiocontrol.

Asymmetric synthesis of dihydrocoumarins via catalytic sequential 1,6-addition/transesterification of α-isocyanoacetates with para-quinone methides.

A catalytic asymmetric synthesis of 3,4-dihydrocoumarins with adjacent tertiary-quaternary stereocenters by 1,6-addition/transesterification cascade reaction of α-isocyanoacetates with

Formal (3 + 4)-Annulation of Propargylic p-Quinone Methides with 2-Indolylmethanols: Synthesis of Polysubstituted Indole-Fused Oxepines.

A novel Brønsted acid catalyzed 1,8-addition mediated (3 + 4)-annulation of in situ generated propargylic p-quinone methides with 2-indolylmethanols is described. This method provides a convenient

Brønsted Acid-Catalyzed Formal (3+3)-Annulation of Propargylic (Aza)-para-Quinone Methides with 4-Hydroxycoumarins and 1,3-Dicarbonyl Compounds.

This methodology affords efficient and practical access to synthetically important and highly functionalized pyranocoumarins and pyrans in excellent yields under mild conditions and exhibit impressive inhibitory activity toward α-glucosidase.

Harnessing Nucleophilicity of Allenol Ester with p-Quinone Methides via Gold Catalysis: Application to the Synthesis of Diarylmethine-Substituted Enones.

A gold(I)-catalyzed protocol for intermolecular 1,6-conjugate addition of nucleophilic allenol ester generated in situ through [3,3]-sigmatropic rearrangement with p-quinone methides ( p-QMs) has

Organocatalytic Asymmetric Addition of Aromatic α-Cyanoketones to o-Quinone Methides: Synthesis of 3,4-Dihydrocoumarins and Tetrasubstituted Chromans.

The first organocatalytic asymmetric addition of aromatic α-cyanoketones to in situ-generated o-quinone methides has been developed. The products 3,4-dihydrocoumarin and tetrasubstituted chroman were

Base-controlled chemoselectivity reaction of vinylanilines with isothiocyanates for synthesis of quinolino-2-thione and 2-aminoquinoline derivatives.

It is reported that a base-controlled chemo-selective reaction of vinylanilines with alkyl/aryl isothiocyanates to afford quinolino-2-thione and 2-aminoquinoline derivatives could be obtained in high yields in the presence of Et3N.
...

References

SHOWING 1-10 OF 84 REFERENCES

Asymmetric Synthesis of 4-Aryl-3,4-dihydrocoumarins by N-Heterocyclic Carbene Catalyzed Annulation of Phenols with Enals.

The highly enantioselective synthesis of 4-aryl-3,4-dihydrocoumarins was realized through direct annulation of phenols with enals catalyzed by dihydroisoquinoline-type NHC (DHIQ-NHC), an

Kinetic resolution of 4-substituted-3,4-dihydrocoumarins via Pd-catalyzed asymmetric allylic alkylation reaction: enantioselective synthesis of trans-3,4-disubstituted-3,4-dihydrocoumarins

The kinetic resolution of 4-substituted-3,4-dihydrocoumarins was realized via Pd-catalyzed allylic substitution reaction using Trost's chiral ligand L12, affording optically active mono- and

Copper-catalyzed enantioselective 1,6-boration of para-quinone methides and efficient transformation of gem-diarylmethine boronates to triarylmethanes.

This is the first enantioselective copper-catalyzed 1,6-conjugate addition of bis(pinacolato)diboron to para-quinone methides, and provides an attractive approach to the construction of optically active gem-diarylmehtine boronic esters.

Direct Asymmetric Synthesis of β-Bis-Aryl-α-Amino Acid Esters via Enantioselective Copper-Catalyzed Addition of p-Quinone Methides

The first enantioselective 1,6-conjugate addition of glycine Schiff bases to para-quinone methides was achieved using a Cu(CH3CN)4BF4/Ph-Foxap catalytic system, and enantiopure unnatural amino alcohols were utilized for the synthesis of novel chiral ligands.

Diastereoselective and Enantioselective Synthesis of Unsymmetric β,β-Diaryl-α-Amino Acid Esters via Organocatalytic 1,6-Conjugate Addition of para-Quinone Methides.

A novel strategy based on phase transfer catalysis for the diastereoselective and enantioselective direct assembly of unsymmetric β,β-diaryl-α-amino acid esters via 1,6-conjugate addition of

Catalytic Asymmetric N-Alkylation of Indoles and Carbazoles through 1,6-Conjugate Addition of Aza-para-quinone Methides.

A new organocatalytic strategy is described in which in-situ generated aza-para-quinone methides are employed as the alkylating reagent, and the intermolecular C-N bond formation with various indole and carbazole nucleophiles proceeded efficiently under mild conditions with excellent enantioselectivity and functional-group compatibility.

Palladium-Catalyzed Addition of Arylboronic Acids to para- Quinone Methides for Preparation of Diarylacetates

A palladium-catalyzed addition of arylboronic acids to para-quinone methides has been developed. The catalytic system employing 4,4′-dimethoxy-2,2′-bipyridine (DMeO-BPy) as ligand and

Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins: asymmetric synthesis of (R)-tolterodine.

Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to coumarins proceeded with high enantioselectivity in the presence of a rhodium catalyst to give the corresponding (R)-4-arylchroman-2-ones in over 99% ee.

Bifunctional squaramide-catalyzed synthesis of chiral dihydrocoumarins via ortho-quinone methides generated from 2-(1-tosylalkyl)phenols.

A bifunctional squaramide-catalyzed reaction of azlactones with o-quinone methides in situ generated from 2-(1-tosylalkyl)-phenols has been successfully developed under basic conditions, providing an

Enantioselective synthesis of dihydrocoumarin derivatives by chiral scandium(III)-complex catalyzed inverse-electron-demand hetero-Diels-Alder reaction.

An asymmetric inverse-electron-demand hetero-Diels-Alder reaction between o-quinone methides and azlactones to generate potentially pharmacological active dihydrocoumarins has been achieved
...