Synthesis of α-CF3-proline derivatives by means of a formal (3 + 2)-cyclisation between trifluoropyruvate imines and Michael acceptors. Issue 23 (31st May 2019)

• Record Type: Journal Article
• Authors: Winter, Michael; Faust, Kirill; Himmelsbach, Markus; Waser, Mario
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 23(2019)
• Page Start: 5731
• Page End: 5735
• Publication Date: 2019-05-31
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob01134j
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The first (3 + 2)-cyclisation of 3, 3, 3-trifluoropyruvate-derived imines and indandione-based Michael acceptors giving spirocyclic α-CF3 -α-proline derivatives was developed. Abstract : We herein report the first formal (3 + 2)-cyclisation between 3, 3, 3-trifluoropyruvate-derived imines and indandione-based Michael acceptors. This reaction gives access to a novel class of spirocyclic α-CF3 -α-proline derivatives with complete control of the diastereoselectivity under phase transfer-catalysed reaction conditions.