☆ 4.7 Article

Friedel-Crafts Reaction of Indoles with Isatin-Derived β,γ-Unsaturated α-Keto Esters Using a BINOL-Derived Bisoxazoline (BOX)/Copper(II) Complex as Catalyst

ADVANCED SYNTHESIS & CATALYSIS (2016)

期刊

ADVANCED SYNTHESIS & CATALYSIS

卷 358, 期 19, 页码 3100-3112

出版社

WILEY-V C H VERLAG GMBH

DOI: 10.1002/adsc.201600272

关键词

asymmetric Friedel-Crafts reaction; 3,3 '-bisindoles; indoles; isatin-derived beta,gamma-unsaturated alpha-keto esters; 3-keto ester-3-indolyloxindoles

类别

Chemistry, Applied Chemistry, Organic

资金

National Natural Science Foundation of China [21272166, 21572150]
Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions [13KJA150004]
Program for New Century Excellent Talents in University [NCET-12-0743]
Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)

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摘要

Several chiral BINOL-derived bisoxazoline (BOX)/copper(II) complexes were synthesized and evaluated as catalysts for the Friedel-Crafts reaction of indoles with isatin-derived beta,gamma-unsaturated a-keto esters. The resulting bis-indole products bearing a quaternary stereocenter were obtained in excellent yields and enantioselectivities. Additionally, the desired products were practically transformed to alpha-amino esters, a-hydroxy esters and alpha-keto amides. It is noteworthy that this catalytic procedure was conducted with a catalyst loading of 0.5 mol% without any discernible decrease in the reactivity or enantioselectivity.

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