Construction of Vicinal Tetrasubstituted Stereogenic Centers via a Mannich‐Type Organocatalyzed Addition of Δ2‐Pyrrolin‐4‐ones to Isatin Imines. Issue 6 (15th January 2018)

• Record Type: Journal Article
• Authors: Ričko, Sebastijan; Meden, Anže; Ciber, Luka; Štefane, Bogdan; Požgan, Franc; Svete, Jurij; Grošelj, Uroš
• Is Part Of: Advanced synthesis & catalysis. Volume 360:Issue 6(2018)
• Page Start: 1072
• Page End: 1076
• Publication Date: 2018-01-15
• Subjects: amino acids -- asymmetric organocatalysis -- tetrasubstituted stereocenters -- Mannich reaction -- pyrrolin-4-ones; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201701384
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: Racemic Δ 2 ‐pyrrolin‐4‐ones ( i. e . 4‐pyrrolones), easily available in two steps from N ‐protected α ‐amino acids, undergo organocatalysed asymmetric Mannich‐type addition to isatin‐derived ketimines to furnish the non‐racemic oxindole‐Δ 2 ‐pyrrolin‐4‐one adducts, stereoselectively (up to 96% ee, dr ≥15:1). The oxindole–pyrrolone products feature vicinal tetrasubstituted carbon stereocenters. The developed protocol has a broad substrate scope and tolerates diverse substituents at position C‐5 in 4‐pyrrolones and at positions N‐1 and C‐5/7 in isatin imines. Abstract :