Direct, Palladium-Catalyzed, Multicomponent Synthesis of β-Lactams from Imines, Acid Chloride, and Carbon Monoxide

Dhawan, Rajiv; Dghaym, Rania D.; St‐Cyr, Daniel J.; Arndtsen, Bruce A.

doi:10.1021/ol061308j

Cited by 76 publications

(28 citation statements)

References 39 publications

(27 reference statements)

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“…29 A new palladiumcatalyzed synthesis of 3-amido-substituted β-lactams was reported by Arndtsen and co-workers in 2006. 30 This process involves the one-pot coupling of four components, two imines, CO, and an acid chloride, providing a flexible route to construct β-lactams. Notably, two different imines can be used for the generation of lactams, making the independent control of all the separate substituents possible (Scheme 7b).…”

Section: Palladium-catalyzed Carbonylative Synthesis Of Four-memberedmentioning

confidence: 99%

Synthesis of Heterocycles via Palladium-Catalyzed Carbonylations

2012

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Besides the mentioned processes, palladium-catalyzed carbonylation of alkynols represents another powerful methodology for the preparation of lactones. As early as in 1994, Gabriele and co-workers presented a PdI 2 /KI-catalyzed oxidative carbonylation of α-substituted hydroxyalkynes to four-membered lactones in good yields under mild conditions. Later on, they extended this methodology to but-3-yn-1-ols for the synthesis of five-membered lactones (Scheme 4a). 13 Scheme 1. Selected Examples of Heterocyclic Drugs Scheme 2. Palladium-Catalyzed Carbonylative Synthesis of Lactones Scheme 3. Palladium-Catalyzed Carbonylative Synthesis of Lactones from Alkenyloxiranes Scheme 4. Palladium-Catalyzed Carbonylative Synthesis of Lactones from Alkynols Chemical Reviews Review dx.

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Section: Palladium-catalyzed Carbonylative Synthesis Of Four-memberedmentioning

confidence: 99%

Synthesis of Heterocycles via Palladium-Catalyzed Carbonylations

2012

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“…此后, 他们利用这种方法成功合成并分离出了慕尼黑酮, 并通过醇解得到酰基氨基酸酯 5 [17] . 接着, 他们在后续的研究工作中, 合成了一系列慕尼黑酮环加成反应衍生物, 包括与炔类反应生成吡咯 6 [18] 、与亚胺反应生成 β-内酰胺 7 [19] 、与 N-对甲苯磺酰基亚胺反应生成吡唑 8 [20] (Scheme 3). 这个方法也是最近广受关注的多组 915 2011 年, Arndtsen [22] …”

Section: 验最好在无水无氧的条件下进行unclassified

Recent Progresses in the Chemistry of Münchnones

Miao¹,

Sun²

2016

Chin. J. Org. Chem.

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Münchnones are mesoionic five-membered heterocycles, which play an important role in heterocycles as well as in organic chemistry. Since they were discovered by Huisgen in 1964, there has been growing interest in syntheses, properties and application of münchnones. One of the most significant properties of münchnones is that they can undergo cycloaddition reactions to unsaturated bonds as 1,3-dipoles. This reaction has become an important method for the synthesis of pyrroles and other heterocycles. Recently, remarkable progresses have been achieved in the synthesis of münchnones by means of organometallic reactions, the new reactive properties of münchnones have also been explored, and the application of münchnones in organic synthesis has been widely reported. In this review, these recent progresses in the chemistry of münchnone are summarized.

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“…(8)]. [36] Notably, these are the same components employed to generate imidazoline carboxylates [Eq. (2)].…”

Section: B-lactamsmentioning

confidence: 99%

Metal‐Catalyzed One‐Step Synthesis: Towards Direct Alternatives to Multistep Heterocycle and Amino Acid Derivative Formation

Arndtsen

2008

Chemistry A European J

130

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The growing understanding of transition-metal catalysis has provided the opportunity to design reactions that convert simple, readily available building blocks in one step into an array of biologically relevant products. Described herein is the application of this approach to the construction of various biologically relevant products, including pyrroles, imidazoles, beta-lactams, oxazoles, alpha-amino acids, propargyl amides, functionalized pyridines, and others. These catalytic reactions rely upon several synthetic operations occurring in sequence, in which the reactivity of transition-metal complexes both activates basic building blocks towards reaction, and controls how multiple versions of these substrates come together. Overall, this allows the synthesis of each these products in one step, in high yield, with minimal waste, and with straightforward access to product diversity.

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Direct, Palladium-Catalyzed, Multicomponent Synthesis of β-Lactams from Imines, Acid Chloride, and Carbon Monoxide

Cited by 76 publications

References 39 publications

Synthesis of Heterocycles via Palladium-Catalyzed Carbonylations

Synthesis of Heterocycles via Palladium-Catalyzed Carbonylations

Recent Progresses in the Chemistry of Münchnones

Metal‐Catalyzed One‐Step Synthesis: Towards Direct Alternatives to Multistep Heterocycle and Amino Acid Derivative Formation

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