Intra- and intermolecular hetero-Diels-Alder reactions. 45. Simple and induced diastereoselectivity in intramolecular hetero-Diels-Alder reactions of 1-oxa-1,3-butadienes. Experimental data and calculations

Tietze, Lutz F.; Geissler, Holger; Fennen, Jens; Brumby, Thomas; Brand, S.; Schulz, Gerhard

doi:10.1021/jo00080a030

Cited by 60 publications

(29 citation statements)

References 2 publications

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“…They can also be promoted by Lewis acids, allowing the domino sequence to proceed at lower temperatures. Enantiomerically pure products can also be obtained through the use of enantiomerically pure aldehydes155 or 1,3‐dicarbonyl compounds,156 or in the presence of chiral Lewis acids 157. For all these reasons, the range of applications of this sequence is very large, especially in the field of natural product synthesis.…”

Section: Mcrs Based On the Knoevenagel Reactionmentioning

confidence: 99%

Utilisation of 1,3‐Dicarbonyl Derivatives in Multicomponent Reactions

2004

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Although isocyanide‐based multicomponent reactions (MCRs), introduced in 1921 by Passerini, largely predominate nowadays in the construction of widely diverse heterocycles, one of the first substrate classes involved in a MCR was that of 1,3‐dicarbonyl derivatives, with Hantzsch’s dihydropyridine synthesis appearing as early as 1882. The aim of this microreview is to present an overview of the great synthetic potential of MCRs involving the specific reactivity of easily accessible 1,3‐dicarbonyl derivatives and to stress their more recent utilisation for the development of new and useful methodologies valuable for the selective construction of highly functionalised small organic molecules of high synthetic and biological value. After a short general introduction, we present chronologically the different methodologies developed on the bases of the reactivity of 1,3‐dicarbonyl systems towards many other substrates involved in a variety of synthetic pathways, including Knoevenagel condensations, Michael and Mannich reactions, cyclodehydrations, electrocyclisations, cycloadditions and metal‐promoted transformations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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Section: Mcrs Based On the Knoevenagel Reactionmentioning

confidence: 99%

Utilisation of 1,3‐Dicarbonyl Derivatives in Multicomponent Reactions

2004

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“…The aromatic and aliphatic annulated tetracycles 6 and 7 were prepared according to published procedures. [7] The bridged heterocycle 8 was obtained by a domino-Knoevenagel-hetero-DielsϪAlder reaction of 2-(2-methylallyloxy)-5-methoxybenzaldehyde (1c) and N,NЈ-dimethylbarbituric acid (2) in 91% yield.…”

Section: Resultsmentioning

confidence: 99%

Regioselective Reduction and Ring Cleavage of Polycyclic Barbituric Acid Analogues Derived from Intramolecular Hetero-Diels−Alder Reactions

et al. 2001

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“…Thus, reaction of 27 led to 28 nearly exclusively. In a similar way the aldehydes 29, 31 and 33 yielded the products 30, 32 and 34, respectively, with excellent simple and induced diastereoselectivity (Scheme 5.6) [16]. This procedure has been used for the synthesis of deoxyloganin, an important intermediate in the biogenesis of indole alkaloids [17].…”

Section: Two-component Reactions With An Intramolecular Cycloadditionmentioning

confidence: 88%