The effect of .beta.-dialkylamino substitution on ketone enolization

Pratt, Norman E.; Albizati, Kim F.

doi:10.1021/jo00289a068

Cited by 10 publications

(3 citation statements)

References 2 publications

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“…39 d). [42c] The fact that the deprotonation takes place in a highly regioselective manner at the sterically more hindered aposition may be explained by the acidifying À I effect of the dimethylamino group, [44] which may be substantially reinforced by complexation of the nitrogen with the silicon. For derivatives of acyclic ketones such as 38 b, a cyclic transition state 40 b has been postulated, which allows an intramolecular deprotonation.…”

Section: Silyl Enol Ethersmentioning

confidence: 99%

Modern Variants of the Mannich Reaction

Arend

Westermann

Risch

1998

Angewandte Chemie International Edition

1,095

362

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Important building blocks for the synthesis of drugs or natural products are found in Mannich bases and their derivatives. Modern variants of the Mannich reaction that expand the potential of the classical intermolecular reaction significantly and enable efficient control of the regioselectivity and stereoselectivity are therefore the topic of intensive research. Intramolecular reactions, in particular as part of domino reaction sequences, often afford astoundingly simple and elegant approaches to complex target compounds.

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Section: Silyl Enol Ethersmentioning

confidence: 99%

Modern Variants of the Mannich Reaction

Arend

Westermann

Risch

1998

Angewandte Chemie International Edition

1,095

362

View full text Add to dashboard Cite

show abstract

“…A comparison of the yield of 15c (48 %) with that of 15g (63 %) obtained by the one‐pot method allows us to conclude that the difference of 15 % corresponds to the minor regioisomer SEE3b ( SEE3a / SEE3b , 85:15), which is unable to undergo a 4‐(enol‐ exo )‐ endo ‐trig cyclization, and after workup yields the starting keto lactam 14c . It is also worth mentioning that silyl enol ethers SEE are mixtures of geometric isomers …”

Section: Resultsmentioning

confidence: 99%

“…It is also worth mentioning that silyl enol ethers SEE are mixtures of geometric isomers. [15] Scheme 3. Plausible mechanisms for the intramolecular keto lactam condensation leading to vinylogous lactams.…”

Section: Mechanistic Considerationsmentioning

confidence: 99%

Intramolecular Keto Lactam Condensation: A Convenient and Straightforward Approach to Bicyclic Vinylogous Lactams

Huang

Fan

2017

Eur J Org Chem

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Abstract:Although the aldol condensation is a well-known reaction, the aza-type aldol condensation, namely, the intramolecular condensation of common keto lactams leading to bicyclic vinylogous lactams, is a highly demanding transformation, with potential applications in both organic synthesis and medicinal chemistry. The known methods for this type of cyclization require several steps. In this paper, we disclose a straightforward approach that consists of the in-situ formation of silyl

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Moderne Varianten der Mannich-Reaktion

Arend¹,

Westermann²,

Risch³

1998

Angewandte Chemie

203

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Begehrte Bausteine für die Synthese von Wirk‐ oder Naturstoffen sind Mannich‐Basen und deren Derivate. Moderne Varianten der Mannich‐Reaktion, die die Bandbreite der klassischen intermolekularen Reaktion deutlich erweitern und eine effektive Kontrolle der Regio‐ und Stereoselektivität ermöglichen, sind daher Gegenstand intensiver Forschung. Intramolekulare Reaktionen, insbesondere als Teil von Dominoreaktionssequenzen, führen häufig verblüffend einfach und elegant zu komplexen Zielverbindungen.

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The effect of .beta.-dialkylamino substitution on ketone enolization

Cited by 10 publications

References 2 publications

Modern Variants of the Mannich Reaction

Modern Variants of the Mannich Reaction

Intramolecular Keto Lactam Condensation: A Convenient and Straightforward Approach to Bicyclic Vinylogous Lactams

Moderne Varianten der Mannich-Reaktion

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