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Literature DB >> 21688863

Catalytic asymmetric conjugate allylation of coumarins.

Yulong Kuang¹, Xiaohua Liu, Lu Chang, Min Wang, Lili Lin, Xiaoming Feng.

Abstract

A catalytic asymmetric conjugate allylation was successfully developed to synthesize potential pharmacologically active 4-allyl-2-oxochroman skeletons. A dual activation strategy was employed by using N,N'-dioxide-Yb(OTf)(3) to activate coumarins and using (CuOTf)(2)•C(7)H(8) to activate tetraallyltin via transmetalation, respectively. Good yields and enantioselectivities were obtained under mild conditions.

Entities: Chemical

Year: 2011 PMID： 21688863 DOI： 10.1021/ol201312y

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

10 in total

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Authors: Kun Liu; M Todd Hovey; Karl A Scheidt
Journal: Chem Sci Date: 2014-10-01 Impact factor: 9.825

2. Catalytic Enantioselective Conjugate Additions of (pin)B-Substituted Allylcopper Compounds Generated in situ from Butadiene or Isoprene.

Authors: Xiben Li; Fanke Meng; Sebastian Torker; Ying Shi; Amir H Hoveyda
Journal: Angew Chem Int Ed Engl Date: 2016-07-20 Impact factor: 15.336

3. Catalytic Enantioselective Addition of an Allyl Group to Ketones Containing a Tri-, a Di-, or a Monohalomethyl Moiety. Stereochemical Control Based on Distinctive Electronic and Steric Attributes of C-Cl, C-Br, and C-F Bonds.

Authors: Diana C Fager; KyungA Lee; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2019-09-25 Impact factor: 15.419

4. N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.

Authors: Anna Lee; Karl A Scheidt
Journal: Chem Commun (Camb) Date: 2015-02-25 Impact factor: 6.222

5. Synthesis of Quaternary Carbon Stereogenic Centers by Diastereoselective Conjugate Addition of Boron-Stabilized Allylic Nucleophiles to Enones.

Authors: Michael Z Liang; Simon J Meek
Journal: J Am Chem Soc Date: 2020-05-18 Impact factor: 15.419

6. Racemic Vinylallenes in Catalytic Enantioselective Multicomponent Processes: Rapid Generation of Complexity through 1,6-Conjugate Additions.

Authors: Youming Huang; Sebastian Torker; Xinghan Li; Juan Del Pozo; Amir H Hoveyda
Journal: Angew Chem Int Ed Engl Date: 2019-02-06 Impact factor: 15.336

Catalytic asymmetric conjugate allylation of coumarins.

1. A Cooperative N-Heterocyclic Carbene/Palladium Catalysis System.

2. Catalytic Enantioselective Conjugate Additions of (pin)B-Substituted Allylcopper Compounds Generated in situ from Butadiene or Isoprene.

3. Catalytic Enantioselective Addition of an Allyl Group to Ketones Containing a Tri-, a Di-, or a Monohalomethyl Moiety. Stereochemical Control Based on Distinctive Electronic and Steric Attributes of C-Cl, C-Br, and C-F Bonds.

4. N-Heterocyclic carbene-catalyzed enantioselective annulations: a dual activation strategy for a formal [4+2] addition for dihydrocoumarins.

5. Synthesis of Quaternary Carbon Stereogenic Centers by Diastereoselective Conjugate Addition of Boron-Stabilized Allylic Nucleophiles to Enones.

6. Racemic Vinylallenes in Catalytic Enantioselective Multicomponent Processes: Rapid Generation of Complexity through 1,6-Conjugate Additions.

7. Synthesis of Coumarin and Homoisoflavonoid Derivatives and Analogs: The Search for New Antifungal Agents.

8. Titanium(IV)-catalyzed stereoselective synthesis of spirooxindole-1-pyrrolines.

9. Catalytic enantioselective 1,6-conjugate additions of propargyl and allyl groups.

10. Photochemical Organocatalytic Regio- and Enantioselective Conjugate Addition of Allyl Groups to Enals.