Synthesis 2014; 46(05): 537-585
DOI: 10.1055/s-0033-1340615
review
© Georg Thieme Verlag Stuttgart · New York

Dimethyl Acetylenedicarboxylate: A Versatile Tool in Organic Synthesis

Constantinos G. Neochoritis
Department of Chemistry, Laboratory of Organic Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Macedonia, Greece   Fax: +30(2310)997679   Email: ioulia@chem.auth.gr
,
Tryfon Zarganes-Tzitzikas
Department of Chemistry, Laboratory of Organic Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Macedonia, Greece   Fax: +30(2310)997679   Email: ioulia@chem.auth.gr
,
Julia Stephanidou-Stephanatou*
Department of Chemistry, Laboratory of Organic Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Macedonia, Greece   Fax: +30(2310)997679   Email: ioulia@chem.auth.gr
› Author Affiliations
Further Information

Publication History

Received: 03 October 2013

Accepted after revision: 05 November 2013

Publication Date:
07 February 2014 (online)


Abstract

This review presents the recent progress in the chemistry of dimethyl acetylenedicarboxylate (DMAD). The interest in and applications of this powerful reagent with more than 135 years of history have greatly increased in the last 10 years, further proving its versatility. Undoubtedly, DMAD can be a multi-tool in the quest of molecular complexity and diversity. The extreme structural diversity of the products described in this review illustrates the powerful potential of DMAD as a building block in organic synthesis.

1 Introduction

2 Michael Reactions

2.1 Sulfur as Nucleophile

2.2 Nitrogen as Nucleophile

2.3 Oxygen as Nucleophile

2.4 Addition to Carbon–Carbon Double Bonds

3 Cycloaddition Reactions

3.1 Diels–Alder Reactions ([4+2] Cycloadditions)

3.2 1,3-Dipolar Reactions ([3+2] Cycloadditions)

3.3 [2+2] Cycloadditions

3.4 [8+2] Cycloadditions

4 DMAD and the Generation of Zwitterions; Multicomponent Reactions (MCRs)

4.1 Phosphines and Derivatives

4.2 Amines

4.3 Isocyanides

4.4 Carbenes

4.5 Miscellaneous Reactions

5 Conclusion

 
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