Four‐Component One‐Pot Process Involving Passerini Reaction Followed by Aldol Addition and Transesterification. Issue 23 (16th March 2020)

• Record Type: Journal Article
• Authors: Hasan, Muhammad; Zaman, Manzoor; Peshkov, Anatoly A.; Amire, Niyaz; Les, Adil; Nechaev, Anton A.; Wang, Yuqing; Kashtanov, Stepan; Van der Eycken, Erik V.; Pereshivko, Olga P.; Peshkov, Vsevolod A.
• Is Part Of: European journal of organic chemistry. Issue 23(2020)
• Page Start: 3378
• Page End: 3389
• Publication Date: 2020-03-16
• Subjects: Aldol addition -- Multicomponent reactions -- Passerini reaction -- Transesterification -- Molecular diversity; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000015
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A four‐component one‐pot transformation involving the Passerini reaction, an aldol addition, and a transesterification has been elaborated, providing an access to a library of densely functionalized tartaric acid derivatives. Two modifications of the process have been explored. In the first modification, carboxylic acids and isocyanides were treated with an excess of ethyl glyoxalate leading to the incorporation of two ethyl glyoxalate residues in the resulting post‐Passerini products. The second modification involved the initial reaction of a carboxylic acid, an aryl glyoxal and an isocyanide to form the Passerini adduct. This was followed by the in situ addition of ethyl glyoxalate to produce the second type of post‐Passerini products through aldol addition and transesterification. Abstract : A four‐component one‐pot transformation involving the Passerini reaction, an aldol addition, and a transesterification has been elaborated, providing an access to a library of densely functionalized tartaric acid derivatives. The overall process can be regarded as an isocyanide‐triggered benzoin‐type condensation. Consequently, two modifications of the process have been developed – a homo‐condensation of ethyl glyoxalate and a cross‐condensation of aryl glyoxal with ethyl glyoxalate.