Asymmetric organocatalytic direct Mannich reaction of acetylacetone and isatin derived ketimines: Low catalyst loading in chiral cinchona-squaramides
TETRAHEDRON LETTERS, cilt.59, sa.6, ss.541-545, 2018 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 59 Sayı: 6
- Basım Tarihi: 2018
- Doi Numarası: 10.1016/j.tetlet.2017.12.081
- Dergi Adı: TETRAHEDRON LETTERS
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Sayfa Sayıları: ss.541-545
- Anahtar Kelimeler: Asymmetric organocatalysis, Mannich reaction, 3-Amino-2-oxindole, Isatin ketimine, Bifunctional squaramide, ENANTIOSELECTIVE MICHAEL ADDITION, PICTET-SPENGLER REACTIONS, AZA-HENRY REACTION, CONJUGATE ADDITION, ALPHA-AMINATION, CHEMICAL SPACE, CONTIGUOUS STEREOCENTERS, RECEPTOR ANTAGONIST, DERIVATIVES, 3-AMINOOXINDOLES
- Orta Doğu Teknik Üniversitesi Adresli: Evet
Özet
A highly enantioselective synthesis of 3-amino-2-oxindoles by direct Mannich reaction between acetylacetone and N-carbamoyl isatin ketimine has been described herein. Corresponding chiral adducts were obtained in high yields (up to 98%) and with excellent enantioselectivities (up to >99% ee) by very low (1 mol%) catalyst loading of 2-adamantyl substituted bifunctional cinchona-squaramide. (C) 2017 Elsevier Ltd. All rights reserved.