Recent advances of asymmetric catalytic transformations of alkylidene Meldrum's acid derivatives
- PMID: 40227105
- DOI: 10.1039/d5cc01032b
Recent advances of asymmetric catalytic transformations of alkylidene Meldrum's acid derivatives
Abstract
Amongst the electron-deficient alkene derivatives, as molecular platforms widely used in organic synthesis, the readily available alkylidene Meldrum's acid derivatives hold a unique place due to the high electrophilicity and chemical versatility of the 1,3-dioxan-4,6-dione moiety. This short review intends to give an overview of recent advances in the asymmetric catalytic transformation of alkylidene Meldrum's acids into valuable chiral heterocycles, evolving from seminal investigations into C-C bond construction from the alkene moiety, to more recent enantioselective C-N and C-S bond formation, vinylogous processes, and the exploitation of the reactivity of the 1,3-dioxan-4,6-dione moiety to develop efficient annulation sequences.
Similar articles
-
Meldrum's acids and 5-alkylidene Meldrum's acids in catalytic carbon-carbon bond-forming processes.Acc Chem Res. 2010 Mar 16;43(3):440-54. doi: 10.1021/ar900229z. Acc Chem Res. 2010. PMID: 20000793
-
Alkylidene Meldrum's Acids as Platforms for the Vinylogous Synthesis of Dihydropyranones.Angew Chem Int Ed Engl. 2021 May 10;60(20):11110-11114. doi: 10.1002/anie.202014489. Epub 2021 Apr 6. Angew Chem Int Ed Engl. 2021. PMID: 33667024
-
Yb(OTf)3-catalyzed reactions of 5-alkylidene Meldrum's acids with phenols: one-pot assembly of 3,4-dihydrocoumarins, 4-chromanones, coumarins, and chromones.J Org Chem. 2006 Jan 6;71(1):409-12. doi: 10.1021/jo052000t. J Org Chem. 2006. PMID: 16388672
-
Selected applications of Meldrum's acid - a tutorial.Org Biomol Chem. 2021 Jun 16;19(23):5014-5027. doi: 10.1039/d1ob00395j. Org Biomol Chem. 2021. PMID: 34019615 Review.
-
One hundred years of Meldrum's acid: advances in the synthesis of pyridine and pyrimidine derivatives.Mol Divers. 2009 Nov;13(4):399-419. doi: 10.1007/s11030-009-9136-x. Epub 2009 Apr 21. Mol Divers. 2009. PMID: 19381852 Review.
Publication types
LinkOut - more resources
Full Text Sources