Enantioselective Michael Addition of 3-Aryl-Substituted Oxindoles to Methyl Vinyl Ketone Catalyzed by a Binaphthyl-Modified Bifunctional Organocatalyst

Lee, Hyun Joo; Woo, Saet Byeol; Kim, Dae Young

doi:10.3390/molecules17067523

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Enantioselective Michael Addition of 3-Aryl-Substituted Oxindoles to Methyl Vinyl Ketone Catalyzed by a Binaphthyl-Modified Bifunctional Organocatalyst

Lee, Hyun Joo;
Woo, Saet Byeol;
Kim, Dae Young

Citations

WEB OF SCIENCE

27

Citations

SCOPUS

29

초록

The enantioselective conjugate addition reaction of 3-aryl-substituted oxindoles with methyl vinyl ketone promoted by binaphthyl-modified bifunctional organocatalysts was investigated. The corresponding Michael adducts, containing a quaternary center at the C3-position of the oxindoles, were generally obtained in high yields with excellent enantioselectivities (up to 91% ee).

키워드

oxindole; methyl vinyl ketone; conjugate addition; bifunctional organocatalysis; asymmetric catalysis; MANNICH-TYPE REACTIONS; ELECTROPHILIC ALPHA-AMINATION; FLUORO-BETA-KETOESTERS; CONJUGATE ADDITION; ASYMMETRIC-SYNTHESIS; ALPHA,BETA-UNSATURATED KETONES; QUATERNARY STEREOCENTERS; 3-SUBSTITUTED OXINDOLES; CARBENE LIGANDS; ALKYLATION

제목: Enantioselective Michael Addition of 3-Aryl-Substituted Oxindoles to Methyl Vinyl Ketone Catalyzed by a Binaphthyl-Modified Bifunctional Organocatalyst

저자: Lee, Hyun Joo; Woo, Saet Byeol; Kim, Dae Young

DOI: 10.3390/molecules17067523

발행일: 2012-06

유형: Article

저널명: Molecules

권: 17

호: 6

페이지: 7523 ~ 7532

언어: ENG

출판사: Multidisciplinary Digital Publishing Institute (MDPI)

발행국가: 스위스

분량: 10 페이지

ISSN: E 1420-3049
P 1420-3049