Enantioselective addition of diphenyl phosphonate to ketimines derived from isatins catalyzed by binaphthyl-modified organocatalysts

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초록

Chiral binaphthyl-modified squaramide-catalyzed enantioselective addition of diphenyl phosphonate to ketimines derived from isatins has been achieved. This method affords practical and efficient access to chiral 3-amino-3-phosphonyl-substituted oxindole derivatives in high yields with excellent enantioselectivities (up to 99% ee).

키워드

3-amino-3-phosphonyl-substituted oxindole; alpha-aminophosphonates; bifunctional organocatalyst; ketimines; organocatalysis; squaramide; VICINAL TETRASUBSTITUTED STEREOCENTERS; ASYMMETRIC-SYNTHESIS; ALPHA-AMINOPHOSPHONATES; TRANSFER/CYCLIZATION SEQUENCES; NATURAL-PRODUCTS; MANNICH REACTION; BETA-KETOACIDS; AMINO-ACIDS; CONSTRUCTION; TETRAHYDROQUINOLINES
제목
Enantioselective addition of diphenyl phosphonate to ketimines derived from isatins catalyzed by binaphthyl-modified organocatalysts
저자
Jang, Hee Seung; Kim, Yubin; Kim, Dae Young
DOI
10.3762/bjoc.12.149
발행일
2016-07-20
유형
Article
저널명
Beilstein Journal of Organic Chemistry
권
12
페이지
1551 ~ 1556