Synthesis of 1,2‐Amino Alcohols by Sigmatropic Rearrangements of 3‐(N‐Tosylamino)allylic Alcohol Derivatives

Abstract

Sigmatropic rearrangements of 3-(N-tosylamino)allylic alcohol derivatives, a particular subclass of functionalized enamides, have been investigated. Whereas the presence of the nitrogen atom alters the stereochemical outcome of Ireland-Claisen rearrangements of glycolates derived from such substrates, [2,3]-Wittig rearrangements of α-allyloxy acetamides or propargylic ethers derivatives provide access to a wide variety of functionalized 1,2-amino alcohols usually with high levels of stereocontrol, as well as to heterocyclic compounds. The stereoselectivity issues of these rearrangements (1,2-diastereoselectivity, auxiliary-induced diastereoselection, chirality transfer, and double stereodifferentiation) were thoroughly investigated.

Tertiary Enamides as Versatile and Valuable Substrates to Reach Chemical Diversity

“…31 A few years later, Cossy, Meyer, and co-workers thoroughly examined the stereoselectivity issues of [2,3]-Wittig rearrangements and [3,3]-Ireland-Claisen rearrangements. 32…”

Rh-Catalyzed Hydrogenation of Amino Acids to Biobased Amino Alcohols: Tackling Challenging Substrates and Application to Protein Hydrolysates

“…β-Amino alcohols are an interesting class of compounds with a broad range of applications, for instance, as intermediates in the production of pharmaceuticals (e.g., nelfinavir, ethambutol), , as chiral auxiliaries (e.g., pseudoephedrine), and as polymer precursors (e.g., lysinol) . Classical synthetic approaches often start from fossil hydrocarbon resources and consist of multiple steps involving the use of homogeneous catalysts, toxic reagents, and hazardous solvents. ,− Alternatively, the one-step reduction of natural α-amino acids provides a biobased route toward β-amino alcohols, with excellent atom economy for both carbon and nitrogen. Moreover, many amino acids are inexpensive and safe reagents, which are nowadays produced from renewable resources by large-scale fermentation processes ,, or can be recovered from cheap agricultural protein-rich waste, such as animal slaughter waste, algae, sugar beet vinasses, etc .…”

In Silico Prediction of the Toxic Potential of Neuroprotective Bifunctional Molecules Based on Chiral N-Propargyl-1,2-amino Alcohol Derivatives

“…N -Propargylamines and N -propargylamides are synthetic scaffolds widely used by organic chemistry for the preparation of complex bioactive compounds, such as 1,2-amino alcohols, β-amino acids, or polyhydroxylated heterocycles, among others. In this context, we notice that some contributions in the literature report that the N -propargylamine moiety possesses some biochemical activities involved in controlling the cellular redox state, mainly by inhibiting nitric oxide synthase enzymes .…”