Iron(II)-Catalyzed Intramolecular Aminohydroxylation of Olefins with Functionalized Hydroxylamines

Liu, Guansai; Zhang, Yong‐Qiang; Yuan, Yong‐An; Xu, Hao

doi:10.1021/ja311923z

Cited by 152 publications

(56 citation statements)

References 83 publications

(22 reference statements)

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“…Han observed trans difunctionalization of cycloalkenes in the studies of oxime and hydrazone radical addition reactions 4c,d. Recently, Xu reported an iron‐catalyzed method and demonstrated trans selectivity with a cyclohexenyl substrate 4e…”

Section: Methodsmentioning

confidence: 99%

Electrochemical Intramolecular Aminooxygenation of Unactivated Alkenes

Zhu

et al. 2014

Chemistry A European J

103

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An electrochemical approach to the intramolecular aminooxygenation of unactivated alkenes has been developed. This process is based on the addition of nitrogen-centered radicals, generated through electrochemical oxidation, to alkenes followed by trapping of the cyclized radical intermediate with 2,2,6,6-tetramethylpiperidine-N-oxyl radical (TEMPO). Difunctionalization of a variety of alkenes with easily available carbamates/amides and TEMPO affords aminooxygenation products in high yields and with excellent trans selectivity for cyclic systems (d.r. up to>20:1). The approach provides a much-needed complementary route to existing cis-selective methods.

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Section: Methodsmentioning

confidence: 99%

Electrochemical Intramolecular Aminooxygenation of Unactivated Alkenes

Zhu

et al. 2014

Chemistry A European J

103

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“…They are also of great importance as chiral building blocks for chemical synthesis and L - threo -3,4-dihydroxyphenylserine (Droxidopa) is itself a (pro)drug used in the treatment of Parkinson’s disease 5 . Although many different synthetic methods have been reported for their chemical synthesis—including methods based on glycine enolates 6 , glycinamides 7 , glycine Schiff’s base 8 and the aminohydroxylation of olefins 9 —the production of β-hydroxy-α-amino acids by enzymatic means is particularly attractive as these can set two stereocentres in a single reaction that can be performed in a one-pot process with minimal protection of substrates and under mild, aqueous conditions. One such example is found in the threonine aldolases (TAs) although their utility is limited due to low synthetic yields and modest diastereoselectivity (they are highly stereoselective for the α-carbon) 10 11 12 .…”

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confidence: 99%

An L-threonine transaldolase is required for L-threo-β-hydroxy-α-amino acid assembly during obafluorin biosynthesis

et al. 2017

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β-Lactone natural products occur infrequently in nature but possess a variety of potent and valuable biological activities. They are commonly derived from β-hydroxy-α-amino acids, which are themselves valuable chiral building blocks for chemical synthesis and precursors to numerous important medicines. However, despite a number of excellent synthetic methods for their asymmetric synthesis, few effective enzymatic tools exist for their preparation. Here we report cloning of the biosynthetic gene cluster for the β-lactone antibiotic obafluorin and delineate its biosynthetic pathway. We identify a nonribosomal peptide synthetase with an unusual domain architecture and an L-threonine:4-nitrophenylacetaldehyde transaldolase responsible for (2S,3R)-2-amino-3-hydroxy-4-(4-nitrophenyl)butanoate biosynthesis. Phylogenetic analysis sheds light on the evolutionary origin of this rare enzyme family and identifies further gene clusters encoding L-threonine transaldolases. We also present preliminary data suggesting that L-threonine transaldolases might be useful for the preparation of L-threo-β-hydroxy-α-amino acids.

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“…[41][42][43][44][45][46][47][48][49][50][51][52][53] Recently, we discovered dioxazolones can undergo intermolecular N-N coupling with arylamines to make hydrazides under either iridium or iron catalysis. [54][55][56][57][58][59][60][61][62][63][64] Mechanistic studies of the Ir-catalyzed system indicated an outer-sphere nucleophilic attack of the nitrogen group of Ir-nitrenoid intermediate by amine leads to the N-N coupling product.…”

Section: Resultsmentioning

confidence: 99%

Nitrene-Mediated P–N Coupling Under Iron Catalysis

et al. 2022

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P-N and P=N bonds play important roles in the design and synthesis of functional molecules such as bioactive compounds and organic ligands for catalysis. Existing methods for P-N coupling mostly rely on Staudinger condensation or nucleophilic substitution between phosphorus electrophiles and amine nucleophiles. Herein, we report a nitrene-mediated intermolecular P-N coupling reaction between various phosphorus nucleophiles and dioxazolones under simple iron-catalyzed conditions. These reactions offer an efficient, versatile, and broadly applicable method for synthesis of a range of N-P compounds including amidophosphines, iminophosphonamides, phosphinamides, aminophosphines, and iminophosphoranes from readily available precursors under mild conditions.

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Iron(II)-Catalyzed Intramolecular Aminohydroxylation of Olefins with Functionalized Hydroxylamines

Cited by 152 publications

References 83 publications

Electrochemical Intramolecular Aminooxygenation of Unactivated Alkenes

Electrochemical Intramolecular Aminooxygenation of Unactivated Alkenes

An L-threonine transaldolase is required for L-threo-β-hydroxy-α-amino acid assembly during obafluorin biosynthesis

Nitrene-Mediated P–N Coupling Under Iron Catalysis

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