Recent developments in asymmetric multicomponent reactions

Multicomponent reactions (MCRs) receive increasing attention because they address both diversity and complexity in organic synthesis. Thus, in principle diverse sets of relatively complex structures can be generated from simple starting materials in a single reaction step. The ever increasing need f...

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Bibliographic Details
Published inChemical Society reviews Vol. 41; no. 1; pp. 3969 - 49
Main Authors de Graaff, Corien, Ruijter, Eelco, Orru, Romano V. A
Format Journal Article
LanguageEnglish
Published England 21.05.2012
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Summary:Multicomponent reactions (MCRs) receive increasing attention because they address both diversity and complexity in organic synthesis. Thus, in principle diverse sets of relatively complex structures can be generated from simple starting materials in a single reaction step. The ever increasing need for optically pure compounds for pharmaceutical and agricultural applications as well as for catalysis promotes the development of asymmetric multicomponent reactions. In recent years, asymmetric multicomponent reactions have been applied to the total synthesis of various enantiopure natural products and commercial drugs, reducing the number of required reaction steps significantly. Although many developments in diastereoselective MCRs have been reported, the field of catalytic enantioselective MCRs has just started to blossom. This critical review describes developments in both diastereoselective and catalytic enantioselective multicomponent reactions since 2004. Significantly broadened scopes, new techniques, more environmentally benign methods and entirely novel MCRs reflect the increasingly inventive paths that synthetic chemist follow in this field. Until recently, enantioselective transition metal-catalyzed MCRs represented the majority of catalytic enantioselective MCRs. However, metal contamination is highly undesirable for drug synthesis. The emergence of organocatalysis greatly influences the quest for new asymmetric MCRs. This Critical Review presents an overview of recent developments and trends in diastereoselective and catalytic asymmetric multicomponent reactions.
Bibliography:Corien de Graaff studied chemistry at the VU University Amsterdam, where she received her BSc degree in 2009 and her MSc degree cum laude in 2011. In 2011 she started her PhD work in the group of Romano V. A. Orru at the VU University Amsterdam working on asymmetric multicomponent reactions. Her research interests include biocatalysis and organocatalysis.
Romano V. A. Orru studied molecular sciences at the Agricultural University in Wageningen, the Netherlands, where he obtained his PhD in 1994. From 1996 to 2000 he worked in the group of K. Faber at the Technical and Karl-Franszens Universities (Graz, Austria). In 2000 he was appointed assistant professor and later associate professor at the VU University Amsterdam. Since 2007 he is a full professor of synthetic and bioorganic chemistry. His current research focuses on the development of novel diversity-oriented synthetic methodology for the synthesis of pharmaceutically relevant compounds and natural products.
Eelco Ruijter studied chemistry at the VU University Amsterdam, the Netherlands. He obtained his PhD in the group of L. A. Wessjohann at the VU University Amsterdam and the Institute of Plant Biochemistry in Halle, Germany. In 2004, he joined the group of R. M. J. Liskamp at Utrecht University as a postdoctoral fellow working on chemical proteomics. In December 2006, he was appointed assistant professor at the VU University Amsterdam. His research interests include the use of multicomponent and cascade reactions and novel catalytic reactions for the efficient construction of complex small molecules.
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ISSN:0306-0012
1460-4744
DOI:10.1039/c2cs15361k