One-pot catalytic enantioselective synthesis of functionalized tetrahydroquinolines by aza-michael/michael cascade reactions of N-protected 2-aminophenyl α,β-unsaturated esters with Nitroolefins

Synthesis (Germany)

Volumn 46, Issue 24, 2014, Pages 3365-3373

  Kang, Ki Tae ^a   Kim, Sung Gon ^a  

^a Kyonggi University   (South Korea)

Author keywords

asymmetric synthesis; cascade reactions; Michael additions; organocatalysis; tetrahydroquinolines

Indexed keywords

ADDITION REACTIONS; CHELATION; ENANTIOSELECTIVITY; ESTERIFICATION; ESTERS; REACTION KINETICS; SELECTIVE CATALYTIC REDUCTION;

ASYMMETRIC SYNTHESIS; CASCADE REACTIONS; MICHAEL ADDITIONS; ORGANOCATALYSIS; TETRAHYDROQUINOLINES;

SYNTHESIS (CHEMICAL);

1,2,3,4 TETRAHYDROQUINOLINE DERIVATIVE; 2 AMINOPHENYL ALPHA UNSATURATED KETONE; 2 AMINOPHENYL BETA UNSATURATED KETONE; BENZYL(3 NITRO 2 PHENYL 1 TOSYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL)ACETATE; BETA NITROSTYRENE; CINCHONA ALKALOID; ETHYL(2 ISOPROPYL 3 NITRO 1 TOSYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL)ACETATE; ETHYL(3 NITRO 2 PHENYL 1 TOSYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL)ACETATE; ETHYL(6 BROMO 3 NITRO 2 PHENYL 1 TOSYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL)ACETATE; ETHYL(6 CHLORO 3 NITRO 2 PHENYL 1 TOSYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL)ACETATE; ETHYL(6 METHYL 3 NITRO 2 PHENYL 1 TOSYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL)ACETATE; ETHYL(7 CHLORO 3 NITRO 2 PHENYL 1 TOSYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL)ACETATE; ETHYL(7 NITRO 6 PHENYL 5 TOSYL 5,6,7,8 TETRAHYDRO[1,3]DIOXOLO[4,5 G]QUINOLIN 8 YL)ACETATE; ETHYL(8 METHYL 3 NITRO 2 PHENYL 1 TOSYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL)ACETATE; ETHYL[2 (2 BROMOPHENYL) 3 NITRO 1 TOSYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]ACETATE; ETHYL[2 (2 CHLOROPHENYL) 3 NITRO 1 TOSYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]ACETATE; ETHYL[2 (2 METHOXYPHENYL) 3 NITRO 1 TOSYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]ACETATE; ETHYL[2 (3 METHOXYPHENYL) 3 NITRO 1 TOSYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]ACETATE; ETHYL[2 (3,4 DIMETHOXYPHENYL) 3 NITRO 1 TOSYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]ACETATE; ETHYL[2 (4 CHLOROPHENYL) 3 NITRO 1 TOSYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]ACETATE; ETHYL[2 (4 FLUOROPHENYL) 3 NITRO 1 TOSYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]ACETATE; ETHYL[2 (4 METHOXYPHENYL) 3 NITRO 1 TOSYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]ACETATE; ETHYL[3 NITRO 2 (2 THIENYL) 1 TOSYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]ACETATE; ETHYL[3 NITRO 2 (4 NITROPHENYL) 1 TOSYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]ACETATE; ETHYL[3 NITRO 2 (4 TOLYL) 1 TOSYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL]ACETATE; KETONE DERIVATIVE; METHYL(3 NITRO 2 PHENYL 1 TOSYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL)ACETATE; NITRO DERIVATIVE; TERT BUTYL(3 NITRO 2 PHENYL 1 TOSYL 1,2,3,4 TETRAHYDROQUINOLIN 4 YL)ACETATE; UNCLASSIFIED DRUG;

ARTICLE; AZA MICHAEL REACTION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; DIASTEREOSELECTIVITY; DRUG DETERMINATION; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH THROUGHPUT SCREENING; MICHAEL ADDITION; MICHAEL CASCADE REACTION; ORGANOCATALYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

EID: 84915749007     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0034-1379044     Document Type: Article

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