Rhodium-Catalyzed Ring-Opening Reactions of a 3-Aza-2-oxabicyclo[2.2.1]hept-5-ene with Arylboronic Acids

Machin, Ben P.; Ballantine, Melissa; Mandel, Jérémie; Blanchard, Nicolas; Tam, William

doi:10.1021/jo901248w

Cited by 28 publications

(23 citation statements)

References 68 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…range; 14 this is particularly clear by comparing the values for the same alkenes in the reactions with N-phenyltriazolinedione (Ph-TAD) and singlet oxygen ( 1 O 2 ). 15 In fact, tetramethylethylene is 2000 times more reactive than transhex-3-ene in the reaction with Ph-TAD and 2900 times more reactive than trans-hex-3-ene in the reaction with 1…”

Section: Paper Syn Thesismentioning

confidence: 99%

The Easy Approach to N-Hydroxy-N-cycloalkenylamides through Nitrosocarbonyl Ene Reactions to Cycloalkenes: Valuable Compounds for Antiviral Syntheses

et al. 2018

View full text Add to dashboard Cite

An easy approach to N-hydroxy-N-cycloalkenylamides, ene adducts of cyclic alkenes of different sizes, is presented. The products can be obtained both through the thermal generation of the nitrosocarbonyl intermediates and via the photochemical fragmentation of the Wieland heterocycle, this being the mildest way to generate these fleeting species, also affording the best results so far in terms of chemical yields. The use of the ene reaction for the synthesis of biologically active molecules represents an interesting and valuable aspect of modern organic synthesis, and this is the strategy proposed as a remarkable alternative to current methods.

show abstract

Section: Paper Syn Thesismentioning

confidence: 99%

The Easy Approach to N-Hydroxy-N-cycloalkenylamides through Nitrosocarbonyl Ene Reactions to Cycloalkenes: Valuable Compounds for Antiviral Syntheses

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Quite recently, Fan and co‐workers reported a highly active palladium/zinc co‐catalytic system working in neutral reaction conditions without the necessity of a base that was suitable for both oxa‐ and azabenzonorbornadienes [59] . While the ring opening reaction of bicyclic oxazines (i.e 3‐aza‐2‐oxabicyclo[2.2.1]heptenes) with arylboronic acids has been developed only in a racemic fashion using rhodium(I) catalysis, [60] the chemistry of the ring opening of bicyclic hydrazines (i.e 2,3‐diazabicyclo[2.2.1]heptenes) has been studied in much more detail. As regard asymmetric methods, in 2006 Pineschi and co‐workers developed the first rhodium‐catalyzed arylative ring opening of bicyclic hydrazines [61] .…”

Section: Boronic Acids and Derivativesmentioning

confidence: 99%

Boron Reagents and Catalysts for the Functionalization of Strained Heterocycles

Pineschi

2021

Adv Synth Catal

View full text Add to dashboard Cite

The particular nature of boron compounds allows an ample modularity of their properties ranging from Lewis acids, C‐nucleophiles, B‐nucleophiles, or even conjunctive reagents for new synthetic manipulations. Moreover, the increasing demand for functionalized boron derivatives for pharmaceutical or material science applications requires the development of new synthetic methods for boron introduction in organic compounds. This review summarizes the possible combinations of boron derivatives with a variety of strained heterocycles reported in the most recent literature.

show abstract

“…Recently, Tam and co-workers reported their investigation on 3-aza-2-oxabicyclo[2.2.1]heptenes 1d with a large variety of Rh sources as the catalysts in presence of different solvents and bases. The use of [Rh(COD)Cl] 2 , Binap as the ligand, NaHCO 3 in MeOH at 60 °C was found to be optimal conditions to obtain the 1,2-ring opened products regioselectively, albeit as cis/trans mixtures [59] (Scheme 12). A similar catalytic system had previously been reported by our group for the enantioselective desymmetrization of bicyclic hydrazines with aryl boronic acids [57,58,60].…”

Section: Organometallic Reagentsmentioning

confidence: 99%

Stereoselective Ring Opening of Bicyclic Nitroso Diels-Alder Cycloadducts with Carbon Nucleophiles

Crotti¹,

Pineschi

2012

COS

View full text Add to dashboard Cite

Bicyclic oxazines are attractive compounds and valuable synthetic intermediates as they can be easily obtained by hetero Diels-Alder reactions between cyclic dienes and nitroso dienophiles. In particular, the more strained case (i.e. the [2.2.1]-cycloadduct) represents an interesting powerful combination of stability and reactivity as it can be transformed into highly densely functionalized cyclopentene derivatives by a variety of ring-opening reactions. Aim of this article is to summarize the methods used by various chemists for opening of bicyclic oxazines by the formation of a new carbon-carbon bond, to give highly substituted ring systems containing multiple stereocenters. Particular emphasis will be given to regio-and stereoselective procedures, including the most recent developments on less strained [2.2.2]-cycloadduct.

show abstract

Rhodium-Catalyzed Ring-Opening Reactions of a 3-Aza-2-oxabicyclo[2.2.1]hept-5-ene with Arylboronic Acids

Cited by 28 publications

References 68 publications

The Easy Approach to N-Hydroxy-N-cycloalkenylamides through Nitrosocarbonyl Ene Reactions to Cycloalkenes: Valuable Compounds for Antiviral Syntheses

The Easy Approach to N-Hydroxy-N-cycloalkenylamides through Nitrosocarbonyl Ene Reactions to Cycloalkenes: Valuable Compounds for Antiviral Syntheses

Boron Reagents and Catalysts for the Functionalization of Strained Heterocycles

Stereoselective Ring Opening of Bicyclic Nitroso Diels-Alder Cycloadducts with Carbon Nucleophiles

Contact Info

Product

Resources

About