Hydrogen‐Bond‐Directed Highly Stereoselective Synthesis of (Z)‐Enamides via Pd‐Catalyzed Oxidative Amidation of Conjugated Olefins.

Ahn, Doo‐Sik; Jung, Doo Young; Lee, Ji Min; Do, Youngkyu; Kim, Sang Kyu; Chang, Sukbok

doi:10.1002/chin.200705080

Cited by 4 publications

(4 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Similar to the reactions reported in Sections 2.1 and 2.2, the coordination of olefin 2 to Pd(II) leads to a Pd(II) complex VIII. The intermediate VIII is subjected to nucleophilic attack by the primary amine, followed by formation of a six-membered Pd complex IX, possibly by hydrogen bonding between the carbonyl oxygen atom and the hydrogen atom of the primary amine [63]. Subsequently, β-hydride elimination from intermediate VIII generates Pd-H and the Z amination product.…”

Section: Palladium-catalyzed Z-selective Oxidative Amination Of Orthomentioning

confidence: 99%

Palladium-Catalyzed Intermolecular Oxidative Amination of Alkenes with Amines, Using Molecular Oxygen as Terminal Oxidant

Obora

Ishii

2013

Catalysts

View full text Add to dashboard Cite

Abstract:In this review, we summarize recent progress from our group with regard to Pd-catalyzed oxidative amination of alkenes with amines. Intermolecular oxidative amination of alkenes with secondary anilines was induced using a palladium-complex catalyst combined with molybdovanadophosphate as a co-catalyst under dioxygen, leading to allylic amines and enamines in good yields with high selectivities. The reaction proceeded efficiently, using molecular oxygen as the terminal oxidant. In addition, palladium-catalyzed oxidative amination of alkenes with anilines as primary amines was achieved using molecular oxygen as the sole oxidant, producing (Z)-N-alkenyl-substituted anilines in high yields.

show abstract

Section: Palladium-catalyzed Z-selective Oxidative Amination Of Orthomentioning

confidence: 99%

Palladium-Catalyzed Intermolecular Oxidative Amination of Alkenes with Amines, Using Molecular Oxygen as Terminal Oxidant

Obora

Ishii

2013

Catalysts

View full text Add to dashboard Cite

show abstract

“…While the analogue lacked appreciable activity against bacteria such as Escherichia coli and Streptococcus pneumoniae , it was found to inhibit the growth of multidrug‐resistant strains of Staphylococcus aureus with MIC values between 30 and 230 μM (Sugie et al ., 2001). In light of the antibacterial activity of CJ‐15,801, multiple synthetic routes to this compound have since been published (Han et al ., 2004; Nicolaou & Mathison, 2005; Lee et al ., 2006). The synthesis of a series of related enamides has also been reported (Villa et al ., 2007).…”

Section: Pantothenic Acid Analogues As Antibacterial and Antifungal Amentioning

confidence: 99%

Coenzyme A biosynthesis: an antimicrobial drug target

Spry¹,

Kirk²,

Saliba³

2008

FEMS Microbiol Rev

245

260

View full text Add to dashboard Cite

Pantothenic acid, a precursor of coenzyme A (CoA), is essential for the growth of pathogenic microorganisms. Since the structure of pantothenic acid was determined, many analogues of this essential metabolite have been prepared. Several have been demonstrated to exert an antimicrobial effect against a range of microorganisms by inhibiting the utilization of pantothenic acid, validating pantothenic acid utilization as a potential novel antimicrobial drug target. This review commences with an overview of the mechanisms by which various microorganisms acquire the pantothenic acid they require for growth, and the universal CoA biosynthesis pathway by which pantothenic acid is converted into CoA. A detailed survey of studies that have investigated the inhibitory activity of analogues of pantothenic acid and other precursors of CoA follows. The potential of inhibitors of both pantothenic acid utilization and biosynthesis as novel antibacterial, antifungal and antimalarial agents is discussed, focusing on inhibitors and substrates of pantothenate kinase, the enzyme catalysing the rate-limiting step of CoA biosynthesis in many organisms. The best strategies are considered for identifying inhibitors of pantothenic acid utilization and biosynthesis that are potent and selective inhibitors of microbial growth and that may be suitable for use as chemotherapeutic agents in humans.

show abstract

“…For example, oxidative amination reaction of unactivated alkenes with phthalimide can be achieved in high yields, with good regioselectivity for the Markovnikov product, by applying a high pressure of O 2 (Scheme 18, eq. 3) [48]. Conversely, the addition of nucleophilic aromatic amines to electron-deficient olefins required a mixture of molybdovanadophosphoric acid (HPMoV), oxygen and hydroquinone (HQ) as reoxidants, to afford E-enamides (Scheme 18, eq.…”

Section: Oxidative Amination Reactionsmentioning

confidence: 99%

Palladium-Catalyzed Heterofunctionalization of C-H, C=C and C≡ C Bonds

Adrio¹,

Hii²

2011

COC

View full text Add to dashboard Cite

The heterofunctionalisation of C-H, C=C and C C bonds is an important type of transformation that converts readily accessible precursors to valuable intermediates in organic synthesis, particularly when the heteroatom = N or O. The progress in this area of homogeneous catalysis by palladium is described in the current review, covering the period between 2005-early 2010. Asymmetric reactions remain a key challenge in this area, which is highlighted.

show abstract

Hydrogen‐Bond‐Directed Highly Stereoselective Synthesis of (Z)‐Enamides via Pd‐Catalyzed Oxidative Amidation of Conjugated Olefins.

Abstract: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Cited by 4 publications

References 1 publication

Palladium-Catalyzed Intermolecular Oxidative Amination of Alkenes with Amines, Using Molecular Oxygen as Terminal Oxidant

Palladium-Catalyzed Intermolecular Oxidative Amination of Alkenes with Amines, Using Molecular Oxygen as Terminal Oxidant

Coenzyme A biosynthesis: an antimicrobial drug target

Palladium-Catalyzed Heterofunctionalization of C-H, C=C and C≡ C Bonds

Contact Info

Product

Resources

About

Hydrogen‐Bond‐Directed Highly Stereoselective Synthesis of (Z)‐Enamides via Pd‐Catalyzed Oxidative Amidation of Conjugated Olefins.

Abstract: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Cited by 4 publications

References 1 publication

Palladium-Catalyzed Intermolecular Oxidative Amination of Alkenes with Amines, Using Molecular Oxygen as Terminal Oxidant

Palladium-Catalyzed Intermolecular Oxidative Amination of Alkenes with Amines, Using Molecular Oxygen as Terminal Oxidant

Coenzyme A biosynthesis: an antimicrobial drug target

Palladium-Catalyzed Heterofunctionalization of C-H, C=C and C&#x2261; C Bonds

Contact Info

Product

Resources

About

Palladium-Catalyzed Heterofunctionalization of C-H, C=C and C≡ C Bonds