Unusual Coupling Reactions of Aldehydes and Alkynes: A Novel Preparation of Substituted Phthalic Acid Derivatives by Automated Synthesis
Based upon a highly versatile multicomponent methodology, a new one‐pot synthesis of substituted phthalic acid derivatives from α,β‐unsaturated aldehydes was developed. The reaction involves the intermediacy of an acetamidodiene species which undergoes Diels–Alder addition to diethyl acetylenedicarb...
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| Published in | Chemistry : a European journal Vol. 9; no. 10; pp. 2273 - 2281 |
|---|---|
| Main Authors | , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
23.05.2003
WILEY‐VCH Verlag Wiley |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0947-6539 1521-3765 |
| DOI | 10.1002/chem.200204668 |
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| Abstract | Based upon a highly versatile multicomponent methodology, a new one‐pot synthesis of substituted phthalic acid derivatives from α,β‐unsaturated aldehydes was developed. The reaction involves the intermediacy of an acetamidodiene species which undergoes Diels–Alder addition to diethyl acetylenedicarboxylate. The resultant acetamidocyclohexadiene is subject to elimination of acetamide under the reaction conditions to give rise to substituted diethyl phthalates in good yields. This domino condensation–cycloaddition–elimination sequence has been applied to a variety of α,β‐unsaturated aldehydes. Furthermore, we demonstrated the exploitation of parallelized and automated synthesis technology for the rapid screening of reaction conditions and compositions. Detailed studies revealed the catalytic role of the employed acetamide and the occurrence of a stereoselective 1,4‐syn elimination pathway under standard conditions.
A new domino condensation –cycloaddition–elimination sequence for the synthesis of substituted phthalic esters has been developed and subjected to parallelized and automated. The 60‐well Syncore reactor used for the synthesis is depicted with the reaction scheme. |
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| AbstractList | Based upon a highly versatile multicomponent methodology, a new one-pot synthesis of substituted phthalic acid derivatives from alpha,beta-unsaturated aldehydes was developed. The reaction involves the intermediacy of an acetamidodiene species which undergoes Diels-Alder addition to diethyl acetylenedicarboxylate. The resultant acetamidocyclohexadiene is subject to elimination of acetamide under the reaction conditions to give rise to substituted diethyl phthalates in good yields. This domino condensation-cycloaddition-elimination sequence has been applied to a variety of alpha,beta-unsaturated aldehydes. Furthermore, we demonstrated the exploitation of parallelized and automated synthesis technology for the rapid screening of reaction conditions and compositions. Detailed studies revealed the catalytic role of the employed acetamide and the occurrence of a stereoselective 1,4-syn elimination pathway under standard conditions. Based upon a highly versatile multicomponent methodology, a new one‐pot synthesis of substituted phthalic acid derivatives from α , β ‐unsaturated aldehydes was developed. The reaction involves the intermediacy of an acetamidodiene species which undergoes Diels–Alder addition to diethyl acetylenedicarboxylate. The resultant acetamidocyclohexadiene is subject to elimination of acetamide under the reaction conditions to give rise to substituted diethyl phthalates in good yields. This domino condensation–cycloaddition–elimination sequence has been applied to a variety of α , β ‐unsaturated aldehydes. Furthermore, we demonstrated the exploitation of parallelized and automated synthesis technology for the rapid screening of reaction conditions and compositions. Detailed studies revealed the catalytic role of the employed acetamide and the occurrence of a stereoselective 1,4‐ syn elimination pathway under standard conditions. Based upon a highly versatile multicomponent methodology, a new one‐pot synthesis of substituted phthalic acid derivatives from α,β‐unsaturated aldehydes was developed. The reaction involves the intermediacy of an acetamidodiene species which undergoes Diels–Alder addition to diethyl acetylenedicarboxylate. The resultant acetamidocyclohexadiene is subject to elimination of acetamide under the reaction conditions to give rise to substituted diethyl phthalates in good yields. This domino condensation–cycloaddition–elimination sequence has been applied to a variety of α,β‐unsaturated aldehydes. Furthermore, we demonstrated the exploitation of parallelized and automated synthesis technology for the rapid screening of reaction conditions and compositions. Detailed studies revealed the catalytic role of the employed acetamide and the occurrence of a stereoselective 1,4‐syn elimination pathway under standard conditions. A new domino condensation –cycloaddition–elimination sequence for the synthesis of substituted phthalic esters has been developed and subjected to parallelized and automated. The 60‐well Syncore reactor used for the synthesis is depicted with the reaction scheme. Based upon a highly versatile multicomponent methodology, a new one-pot synthesis of substituted phthalic acid derivatives from alpha,beta-unsaturated aldehydes was developed. The reaction involves the intermediacy of an acetamidodiene species which undergoes Diels-Alder addition to diethyl acetylenedicarboxylate. The resultant acetamidocyclohexadiene is subject to elimination of acetamide under the reaction conditions to give rise to substituted diethyl phthalates in good yields. This domino condensation-cycloaddition-elimination sequence has been applied to a variety of alpha,beta-unsaturated aldehydes. Furthermore, we demonstrated the exploitation of parallelized and automated synthesis technology for the rapid screening of reaction conditions and compositions. Detailed studies revealed the catalytic role of the employed acetamide and the occurrence of a stereoselective 1,4-syn elimination pathway under standard conditions.Based upon a highly versatile multicomponent methodology, a new one-pot synthesis of substituted phthalic acid derivatives from alpha,beta-unsaturated aldehydes was developed. The reaction involves the intermediacy of an acetamidodiene species which undergoes Diels-Alder addition to diethyl acetylenedicarboxylate. The resultant acetamidocyclohexadiene is subject to elimination of acetamide under the reaction conditions to give rise to substituted diethyl phthalates in good yields. This domino condensation-cycloaddition-elimination sequence has been applied to a variety of alpha,beta-unsaturated aldehydes. Furthermore, we demonstrated the exploitation of parallelized and automated synthesis technology for the rapid screening of reaction conditions and compositions. Detailed studies revealed the catalytic role of the employed acetamide and the occurrence of a stereoselective 1,4-syn elimination pathway under standard conditions. |
| Author | Beller, Matthias Jiao, Haijun Thurow, Kerstin Gördes, Dirk Stoll, Norbert Wendler, Christian Spannenberg, Anke Neumann, Helfried Jacobi von Wangelin, Axel Klaus, Stefan Krüger, Thomas |
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| Keywords | ORGANIC-SYNTHESIS CATALYSIS DIELS-ALDER REACTIONS STEREOCHEMISTRY REACTIVITY DIENOPHILES organocatalysis 1,4-ELIMINATION automated synthesis ELIMINATIONS Diels-Alder reaction multicomponent reaction domino reaction ANHYDRIDE AMIDES |
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| References_xml | – reference: L. E. Overman , R. L. Freerks , C. B. Petty , L. A. Clizbe , R. K. Ono , G. F. Taylor , P. J. Jessup , J. Am. Chem. Soc. 1981, 103, 2816-2822; – reference: K. Fukui , H. Fujimoto , Bull. Chem. Soc. Jpn. 1966, 39, 2116-2126; – reference: J. Yoshida , S. Suga , K. Itami , Kagaku Kogyo 2002, 53, 6-12; – reference: The aldehyde was prepared according to: E. J. Corey , D. Enders , M. G. Bock , Tetrahedron Lett. 1976, 14, 7-10. – reference: H. Neumann , A. Jacobi von Wangelin , D. Gördes , A. Spannenberg , W. Baumann , M. Beller , Tetrahedron 2002, 58, 2381-2387. – reference: C. F. Huebner , E. Donoghue , J. Org. Chem. 1963, 28, 1732; – reference: N. T. Anh , J. Chem. Soc. Chem. Commun. 1968, 1089; – reference: I. Fleming , Frontier Orbitals and Organic Reactions, Wiley, London, 1976. – reference: Weinreb route: J.-M. Nuzillard , A. Boumendjel , G. Massiot , Tetrahedron Lett. 1981, 29, 3779-3780; – reference: G. Shi , S. Cottens , S. A. Shiba , M. 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| Snippet | Based upon a highly versatile multicomponent methodology, a new one‐pot synthesis of substituted phthalic acid derivatives from α,β‐unsaturated aldehydes was... Based upon a highly versatile multicomponent methodology, a new one‐pot synthesis of substituted phthalic acid derivatives from α , β ‐unsaturated aldehydes... Based upon a highly versatile multicomponent methodology, a new one-pot synthesis of substituted phthalic acid derivatives from alpha,beta-unsaturated... |
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| SubjectTerms | automated synthesis Chemistry Chemistry, Multidisciplinary Diels-Alder reaction domino reaction multicomponent reaction organocatalysis Physical Sciences Science & Technology |
| Title | Unusual Coupling Reactions of Aldehydes and Alkynes: A Novel Preparation of Substituted Phthalic Acid Derivatives by Automated Synthesis |
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