Organocatalytic Enantioselective Construction of Heterocycle-Substituted Styrenes with Chiral Atropisomerism.

Autor:	Li QZ; Shanghai Key Laboratory for Molecular Engineer of Chiral Drugs, School of Chemistry and Chemical Engineering & Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai 200240, P. R. China., Lian PF; Shanghai Key Laboratory for Molecular Engineer of Chiral Drugs, School of Chemistry and Chemical Engineering & Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai 200240, P. R. China., Tan FX; Shanghai Key Laboratory for Molecular Engineer of Chiral Drugs, School of Chemistry and Chemical Engineering & Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai 200240, P. R. China., Zhu GD; Shanghai Key Laboratory for Molecular Engineer of Chiral Drugs, School of Chemistry and Chemical Engineering & Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai 200240, P. R. China., Chen C; Shanghai Key Laboratory for Molecular Engineer of Chiral Drugs, School of Chemistry and Chemical Engineering & Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai 200240, P. R. China., Hao Y; Shanghai Key Laboratory for Molecular Engineer of Chiral Drugs, School of Chemistry and Chemical Engineering & Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai 200240, P. R. China., Jiang W; Shanghai Key Laboratory for Molecular Engineer of Chiral Drugs, School of Chemistry and Chemical Engineering & Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai 200240, P. R. China., Wang XH; Shanghai Key Laboratory for Molecular Engineer of Chiral Drugs, School of Chemistry and Chemical Engineering & Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai 200240, P. R. China., Zhou J; Shanghai Key Laboratory for Molecular Engineer of Chiral Drugs, School of Chemistry and Chemical Engineering & Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai 200240, P. R. China., Zhang SY; Shanghai Key Laboratory for Molecular Engineer of Chiral Drugs, School of Chemistry and Chemical Engineering & Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai 200240, P. R. China.
Jazyk:	angličtina
Zdroj:	Organic letters [Org Lett] 2020 Mar 20; Vol. 22 (6), pp. 2448-2453. Date of Electronic Publication: 2020 Mar 06.
DOI:	10.1021/acs.orglett.0c00659
Abstrakt:	We have developed a novel π-π interaction and dual H-bond concerted control strategy to construct axially chiral naphthylamine heterocycles. With ortho -alkynyl-naphthylamines as the electrophile, indoles and 4-hydroxycoumarins were efficiently employed to construct axially chiral skeletons in good yields and with excellent enantioselectivities (up to 97% enantiomeric excess). Furthermore, the resulting products could be converted to potential squaramides featuring organic catalysts.
Databáze:	MEDLINE
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