2011
DOI: 10.1002/chem.201003265
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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 t… Show more

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Cited by 33 publications
(17 citation statements)
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“…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…”
Section: Scheme 17 [23]-wittig Rearrangement Of Enamides Derivativesmentioning
confidence: 99%
“…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…”
Section: Scheme 17 [23]-wittig Rearrangement Of Enamides Derivativesmentioning
confidence: 99%
“…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 .…”
Section: Introductionmentioning
confidence: 99%
“…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 .…”
mentioning
confidence: 99%