Synthesis of Spiro‐Δ2‐Pyrrolin‐4‐One Pseudo Enantiomers via an Organocatalyzed Sulfa‐Michael/Aldol Domino Sequence. Issue 22 (7th October 2019)

• Record Type: Journal Article
• Authors: Grošelj, Uroš; Ciber, Luka; Gnidovec, Jan; Testen, Žan; Požgan, Franc; Štefane, Bogdan; Tavčar, Gašper; Svete, Jurij; Ričko, Sebastijan
• Is Part Of: Advanced synthesis & catalysis. Volume 361:Issue 22(2019)
• Page Start: 5118
• Page End: 5126
• Publication Date: 2019-10-07
• Subjects: asymmetric catalysis -- pyrrolin-4-one -- organic catalysis -- domino reaction -- spiro compounds; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201900747
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: Δ 2 ‐Pyrrolin‐4‐ones undergo organocatalyzed sulfa‐Michael/aldol domino spirocyclizations with mercaptoacetaldehyde dimer. The products contain three contiguous stereocenters ( ee up to 99%, dr up to 95:5, 25 examples) and can be transformed into analogues of natural products. With the use of a single catalyst, the absolute configuration of the products were determined by the configuration of the exocyclic double bond of the starting material. These results point at the possibility of a widespread use of unsaturated Δ 2 ‐pyrrolin‐4‐ones in various (organo)catalyzed (cascade) transformations for accessing libraries of 3D‐rich pyrrolone‐based (spiro)heterocycles. Abstract :