Synthesis, volume 46, issue 05, pages 537-585
Dimethyl Acetylenedicarboxylate: A Versatile Tool in Organic Synthesis
Publication type: Journal Article
Publication date: 2014-02-07
Catalysis
Organic Chemistry
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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Neochoritis C., Zarganes Tzitzikas T., Zarganes-Tzitzikas T. Dimethyl Acetylenedicarboxylate: A Versatile Tool in Organic Synthesis // Synthesis. 2014. Vol. 46. No. 05. pp. 537-585.
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Neochoritis C., Zarganes Tzitzikas T., Zarganes-Tzitzikas T. Dimethyl Acetylenedicarboxylate: A Versatile Tool in Organic Synthesis // Synthesis. 2014. Vol. 46. No. 05. pp. 537-585.
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TY - JOUR
DO - 10.1055/s-0033-1340615
UR - https://doi.org/10.1055/s-0033-1340615
TI - Dimethyl Acetylenedicarboxylate: A Versatile Tool in Organic Synthesis
T2 - Synthesis
AU - Neochoritis, Constantinos
AU - Zarganes Tzitzikas, Tryfon
AU - Zarganes-Tzitzikas, Tryfon
PY - 2014
DA - 2014/02/07
PB - Thieme
SP - 537-585
IS - 05
VL - 46
SN - 0039-7881
SN - 1437-210X
ER -
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@article{2014_Neochoritis,
author = {Constantinos Neochoritis and Tryfon Zarganes Tzitzikas and Tryfon Zarganes-Tzitzikas},
title = {Dimethyl Acetylenedicarboxylate: A Versatile Tool in Organic Synthesis},
journal = {Synthesis},
year = {2014},
volume = {46},
publisher = {Thieme},
month = {feb},
url = {https://doi.org/10.1055/s-0033-1340615},
number = {05},
pages = {537--585},
doi = {10.1055/s-0033-1340615}
}
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Neochoritis, Constantinos, et al. “Dimethyl Acetylenedicarboxylate: A Versatile Tool in Organic Synthesis.” Synthesis, vol. 46, no. 05, Feb. 2014, pp. 537-585. https://doi.org/10.1055/s-0033-1340615.