Olefin 1,2-difunctionalization has emerged as a popular strategy within modern synthetic chemistry for the synthesis of vicinal amino alcohols and derivatives. The advantage of this approach is the single-step simplicity for rapid diversification, feedstock nature of the olefin starting materials, and the possible modularity of the components. Although there is a vast number of possible iterations of 1,2-olefin difunctionalization, 1,2-amino oxygenation is of particular interest due to the prevalence of both oxygen and nitrogen within pharmaceuticals, natural products, agrochemicals, and synthetic ligands. The Sharpless amino hydroxylation provided seminal results in this field and displayed the value in achieving methods of this nature. However, a vast number of new and novel methods have emerged in recent decades. This review provides a comprehensive review of modern advances in accomplishing 1,2-amino oxygenation of alkenes, 1,3-dienes, alkynes, and allenes that move beyond osmium to a range of other transition metals and more modern strategies such as electrochemical, photochemical, and biochemical reactivity.

Beyond osmium: progress in 1,2-amino oxygenation of alkenes, 1,3-dienes, alkynes, and allenes

This article describes the reaction of ynamides with metallanitrenes generated in the presence of an iodine(III) oxidant. N-(Boc)-Ynamides are converted to oxazolones via a cyclization reaction. The reaction is mediated by a catalytic dirhodium-bound nitrene species that first behaves as a Lewis acid. The oxazolones can be converted in a one pot manner to functionalized oxazolidinones following a regio- and stereoselective oxyamination reaction with the same nitrene reagent generated in stoichiometric amounts.

Reaction of Ynamides with Iminoiodinane-Derived Nitrenes: Formation of Oxazolones and Polyfunctionalized Oxazolidinones

Double Functionalization of Styrenes by Cu-Mediated Assisted Tandem Catalysis

The rhodium(II)-catalyzed oxidative cyclization of glycal 3-carbamates with in situ incorporation of an alcohol nucleophile at the anomeric position provides access to a range of 2-amino sugars having 1,2-trans-2,3-cis stereochemistry, a structural motif present in compounds of medicinal and biological significance such as the streptothricin group of antibiotics and the Chitinase inhibitor allosamidin. All of the diastereomeric d-glycal 3-carbamates have been investigated, revealing significant differences in anomeric stereoselectivity depending on substrate stereochemistry and protecting groups. In addition, some substrates were prone to forming C3-oxidized dihydropyranone byproducts under the reaction conditions. Allal- and gulal 3-carbamates provided uniformly high stereo- and chemoselectivity, while for glucal substrates, acyclic, electron-withdrawing protecting groups at the 4O and 6O positions were required. Galactal 3-carbamates have been the most challenging substrates; formation of their amidogly...

Glycal Metallanitrenes for 2-Amino Sugar Synthesis: Amidoglycosylation of Gulal-, Allal-, Glucal-, and Galactal 3-Carbamates.

We herein report a modular strategy, which enables Rh(III)-catalyzed diastereoselective 3,4-amino oxygenation and diamination of 1,3-dienes using different O- and N-nucleophiles in combination with readily available 3-substituted 1,4,2-dioxazolones (78 examples, 37–91% yield). Previous attempts to functionalize the internal double bond rested on the use of plain alcoholic solvents as nucleophilic coupling partners thus dramatically limiting the scope of this transformation. We have now identified hexafluoroisopropanol as a non-nucleophilic solvent that allows the use of diverse nucleophiles and greatly expands the scope, including an unprecedented amino hydroxylation to selectively install valuable, unprotected β-amino alcohols across 1,3-dienes. Moreover, various elaborate alcohols prove to be compatible providing unique access to complex organic molecules. Finally, this method is employed in a series of intramolecular reactions to deliver valuable nitrogen heterocycles as well as γ- and δ-lactones. 

Rh(III)-Catalyzed Intra- and Intermolecular 3,4-Difunctionalization of 1,3-Dienes via Rh(III)-π-Allyl Amidation with 1,4,2-Dioxazolones

Rhodium-catalyzed regio- and stereoselective oxyamination of dienes via tandem aziridination/ring-opening of dienyl carbamates

Regio- and stereoselective oxyamination of dienes through a tandem rhodium-catalysed aziridination-nucleophilic opening affords racemic oxazolidinone derivatives, which undergo a kinetic resolution acylation process with amidine-based catalysts (ABCs) to achieve s values of up to 117. This protocol was applied to the enantioselective synthesis of sphingosine.

Enantioselective Synthesis of Aminodiols by Sequential Rhodium-Catalysed Oxyamination/Kinetic Resolution: Expanding the Substrate Scope of Amidine-Based Catalysis.

A general protocol for the enantioselective synthesis of 3-heterosubstituted-2-amino-1-ols was developed based on metal- free intramolecular regio- and stereoselective diene aziridination and regioselective opening. Kinetic resolution of the resulting (1'-NR1 R2 and 1'-SR)-4-oxazolidinones was performed using ABCs organocatalysts, expanding the application of this methodology.

Enantioselective Synthesis of 3‐Heterosubstituted‐2‐amino‐1‐ols by Sequential Metal‐Free Diene Aziridination/Kinetic Resolution

Opposite regioselectivity is observed depending on the whether Rh2(OAc)4 or bulky Rh2(OPiv)4 is used as a catalyst.

Rhodium-Catalyzed Regio- and Stereoselective Oxyamination of Dienes via Tandem Aziridination/Ring-Opening of Dienyl Carbamates.

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Rhodium-catalyzed regio- and stereoselective oxyamination of dienes via tandem aziridination/ring-opening of dienyl carbamates

Enantioselective Synthesis of Aminodiols by Sequential Rhodium-Catalysed Oxyamination/Kinetic Resolution: Expanding the Substrate Scope of Amidine-Based Catalysis.

Enantioselective Synthesis of 3‐Heterosubstituted‐2‐amino‐1‐ols by Sequential Metal‐Free Diene Aziridination/Kinetic Resolution

Rhodium-Catalyzed Regio- and Stereoselective Oxyamination of Dienes via Tandem Aziridination/Ring-Opening of Dienyl Carbamates.