Three‐Component Domino Knoevenagel/Vinylogous Michael Reaction: Entry to Challenging o‐Terphenyls. Issue 25 (8th March 2018)

• Record Type: Journal Article
• Authors: Grau, Dominik; Grau, Benedikt W.; Hampel, Frank; Tsogoeva, Svetlana B.
• Is Part Of: Chemistry. Volume 24:Issue 25(2018)
• Page Start: 6551
• Page End: 6556
• Publication Date: 2018-03-08
• Subjects: domino reactions -- Knoevenagel reaction -- Michael addition -- multicomponent reactions -- organocatalysis -- o-terphenyls; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201800048
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: An unprecedented organocatalytic three‐component domino Knoevenagel/vinylogous Michael reaction starting from simple enolizable aldehydes, malononitrile, and nitroolefins is reported. This facile two‐step domino process provides a straightforward stereoselective route to multifunctional vinyl malononitrile products (up to 82 % yield, 85:15 d.r.) containing a nitroalkane moiety, and contributes to the development of sustainability and atom economy. The application of the obtained domino products for synthesis of highly functionalized o ‐terphenyls (of high interest for materials science and medicinal chemistry) through subsequent new three‐step domino reaction involving cyclization–tautomerization–aromatization steps, has been demonstrated. Abstract : All‐in‐one synthesis : An unprecedented three‐component domino Knoevenagel/vinylogous Michael reaction, providing a straightforward diastereoselective route to multifunctional vinyl malononitrile products is presented (see scheme). The applications of the new domino products for facile synthesis of highly functionalized o ‐terphenyls through a subsequent new three‐step linear domino process, has been demonstrated.