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Literature DB >> 12696877

Highly enantioselective quinoline synthesis via ene-type cyclization of 1,7-enynes catalyzed by a cationic BINAP-palladium(II) complex.

Abstract

The first highly enantioselective synthesis of a six-membered ring quinoline catalyzed by a cationic BINAP-palladium(II) complex is shown to afford the quinoline products having a quaternary carbon center or a spiro-ring in quantitative yield and >99% ee.

Entities: Chemical

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Year: 2003 PMID： 12696877 DOI： 10.1021/ja0292748

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

10 in total

1. Synthesis of acyclic alpha,beta-unsaturated ketones via Pd(II)-catalyzed intermolecular reaction of alkynamides and alkenes.

Authors: Norie Momiyama; Matthew W Kanan; David R Liu
Journal: J Am Chem Soc Date: 2007-02-06 Impact factor: 15.419

2. Rhodium(I)-catalyzed decarbonylative spirocyclization through C-C bond cleavage of benzocyclobutenones: an efficient approach to functionalized spirocycles.

Authors: Tao Xu; Nikolas A Savage; Guangbin Dong
Journal: Angew Chem Int Ed Engl Date: 2014-01-20 Impact factor: 15.336

3. Enantioselective Tandem Cyclization of Alkyne-Tethered Indoles Using Cooperative Silver(I)/Chiral Phosphoric Acid Catalysis.

Authors: Yugen Zhu; Wei He; Wei Wang; Chloe E Pitsch; Xiaotai Wang; Xiang Wang
Journal: Angew Chem Int Ed Engl Date: 2017-08-23 Impact factor: 15.336

4. Rh(i)-catalyzed dimerization of ene-vinylidenecyclopropanes for the construction of spiro[4,5]decanes and mechanistic studies.

Authors: Chao Ning; Kang-Hua Rui; Yin Wei; Min Shi
Journal: Chem Sci Date: 2022-06-01 Impact factor: 9.969

5. Rhodium-catalyzed asymmetric enyne cycloisomerization of terminal alkynes and formal total synthesis of (-)-platensimycin.

Authors: K C Nicolaou; Ang Li; Shelby P Ellery; David J Edmonds
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

6. Palladium-catalyzed carbocyclization of 1,6-enynes leading to six-membered rings or oxidized five-membered trifluoroacetates.

Authors: Koichi Mikami; Manabu Hatano
Journal: Proc Natl Acad Sci U S A Date: 2004-04-12 Impact factor: 11.205

Highly enantioselective quinoline synthesis via ene-type cyclization of 1,7-enynes catalyzed by a cationic BINAP-palladium(II) complex.

1. Synthesis of acyclic alpha,beta-unsaturated ketones via Pd(II)-catalyzed intermolecular reaction of alkynamides and alkenes.

2. Rhodium(I)-catalyzed decarbonylative spirocyclization through C-C bond cleavage of benzocyclobutenones: an efficient approach to functionalized spirocycles.

3. Enantioselective Tandem Cyclization of Alkyne-Tethered Indoles Using Cooperative Silver(I)/Chiral Phosphoric Acid Catalysis.

4. Rh(i)-catalyzed dimerization of ene-vinylidenecyclopropanes for the construction of spiro[4,5]decanes and mechanistic studies.

5. Rhodium-catalyzed asymmetric enyne cycloisomerization of terminal alkynes and formal total synthesis of (-)-platensimycin.

6. Palladium-catalyzed carbocyclization of 1,6-enynes leading to six-membered rings or oxidized five-membered trifluoroacetates.

7. Catalytic asymmetric synthesis of all-carbon quaternary stereocenters.

8. Asymmetric synthesis of medium-sized rings by intramolecular Au(I)-catalyzed cyclopropanation.

9. Chiral cyclopentadienylruthenium sulfoxide catalysts for asymmetric redox bicycloisomerization.

10. Reinvestigation of a Catalytic, Enantioselective Alkene Dibromination and Chlorohydroxylation.