Ring-Opening Reactions of Phosphoramidate Heterocycles
We present protocols for the conversion of phosphoramidate heterocycles into 1,3-chloroamines and 1,3-aminoalcohols. For the formation of chloroamines, our optimized protocol involves heating the phosphoramidate starting material with 4 equivalents of HCl in a dioxane/toluene solvent mixture. The substituents on the phosphoramidate starting material have a profound influence on product formation. Phosphoramidates with a variety of aza-heterocyclic substituents engage, but those containing a 5-chloro-8-quinolinol arm are most competent for 1,3-chloroamine formation. Furthermore, only the phosphoramidate cis diastereomers al...
Source: Tetrahedron - October 27, 2023 Category: Chemistry Authors: Annu Anna Thomas Frederick J Seidl Joel T Mague Shyam Sathyamoorthi Source Type: research
Ring-Opening Reactions of Phosphoramidate Heterocycles
We present protocols for the conversion of phosphoramidate heterocycles into 1,3-chloroamines and 1,3-aminoalcohols. For the formation of chloroamines, our optimized protocol involves heating the phosphoramidate starting material with 4 equivalents of HCl in a dioxane/toluene solvent mixture. The substituents on the phosphoramidate starting material have a profound influence on product formation. Phosphoramidates with a variety of aza-heterocyclic substituents engage, but those containing a 5-chloro-8-quinolinol arm are most competent for 1,3-chloroamine formation. Furthermore, only the phosphoramidate cis diastereomers al...
Source: Tetrahedron - October 27, 2023 Category: Chemistry Authors: Annu Anna Thomas Frederick J Seidl Joel T Mague Shyam Sathyamoorthi Source Type: research
Ring-Opening Reactions of Phosphoramidate Heterocycles
We present protocols for the conversion of phosphoramidate heterocycles into 1,3-chloroamines and 1,3-aminoalcohols. For the formation of chloroamines, our optimized protocol involves heating the phosphoramidate starting material with 4 equivalents of HCl in a dioxane/toluene solvent mixture. The substituents on the phosphoramidate starting material have a profound influence on product formation. Phosphoramidates with a variety of aza-heterocyclic substituents engage, but those containing a 5-chloro-8-quinolinol arm are most competent for 1,3-chloroamine formation. Furthermore, only the phosphoramidate cis diastereomers al...
Source: Tetrahedron - October 27, 2023 Category: Chemistry Authors: Annu Anna Thomas Frederick J Seidl Joel T Mague Shyam Sathyamoorthi Source Type: research
Ring-Opening Reactions of Phosphoramidate Heterocycles
We present protocols for the conversion of phosphoramidate heterocycles into 1,3-chloroamines and 1,3-aminoalcohols. For the formation of chloroamines, our optimized protocol involves heating the phosphoramidate starting material with 4 equivalents of HCl in a dioxane/toluene solvent mixture. The substituents on the phosphoramidate starting material have a profound influence on product formation. Phosphoramidates with a variety of aza-heterocyclic substituents engage, but those containing a 5-chloro-8-quinolinol arm are most competent for 1,3-chloroamine formation. Furthermore, only the phosphoramidate cis diastereomers al...
Source: Tetrahedron - October 27, 2023 Category: Chemistry Authors: Annu Anna Thomas Frederick J Seidl Joel T Mague Shyam Sathyamoorthi Source Type: research
Ring-Opening Reactions of Phosphoramidate Heterocycles
We present protocols for the conversion of phosphoramidate heterocycles into 1,3-chloroamines and 1,3-aminoalcohols. For the formation of chloroamines, our optimized protocol involves heating the phosphoramidate starting material with 4 equivalents of HCl in a dioxane/toluene solvent mixture. The substituents on the phosphoramidate starting material have a profound influence on product formation. Phosphoramidates with a variety of aza-heterocyclic substituents engage, but those containing a 5-chloro-8-quinolinol arm are most competent for 1,3-chloroamine formation. Furthermore, only the phosphoramidate cis diastereomers al...
Source: Tetrahedron - October 27, 2023 Category: Chemistry Authors: Annu Anna Thomas Frederick J Seidl Joel T Mague Shyam Sathyamoorthi Source Type: research
Ring-Opening Reactions of Phosphoramidate Heterocycles
We present protocols for the conversion of phosphoramidate heterocycles into 1,3-chloroamines and 1,3-aminoalcohols. For the formation of chloroamines, our optimized protocol involves heating the phosphoramidate starting material with 4 equivalents of HCl in a dioxane/toluene solvent mixture. The substituents on the phosphoramidate starting material have a profound influence on product formation. Phosphoramidates with a variety of aza-heterocyclic substituents engage, but those containing a 5-chloro-8-quinolinol arm are most competent for 1,3-chloroamine formation. Furthermore, only the phosphoramidate cis diastereomers al...
Source: Tetrahedron - October 27, 2023 Category: Chemistry Authors: Annu Anna Thomas Frederick J Seidl Joel T Mague Shyam Sathyamoorthi Source Type: research
Ring-Opening Reactions of Phosphoramidate Heterocycles
We present protocols for the conversion of phosphoramidate heterocycles into 1,3-chloroamines and 1,3-aminoalcohols. For the formation of chloroamines, our optimized protocol involves heating the phosphoramidate starting material with 4 equivalents of HCl in a dioxane/toluene solvent mixture. The substituents on the phosphoramidate starting material have a profound influence on product formation. Phosphoramidates with a variety of aza-heterocyclic substituents engage, but those containing a 5-chloro-8-quinolinol arm are most competent for 1,3-chloroamine formation. Furthermore, only the phosphoramidate cis diastereomers al...
Source: Tetrahedron - October 27, 2023 Category: Chemistry Authors: Annu Anna Thomas Frederick J Seidl Joel T Mague Shyam Sathyamoorthi Source Type: research
Ring-Opening Reactions of Phosphoramidate Heterocycles
We present protocols for the conversion of phosphoramidate heterocycles into 1,3-chloroamines and 1,3-aminoalcohols. For the formation of chloroamines, our optimized protocol involves heating the phosphoramidate starting material with 4 equivalents of HCl in a dioxane/toluene solvent mixture. The substituents on the phosphoramidate starting material have a profound influence on product formation. Phosphoramidates with a variety of aza-heterocyclic substituents engage, but those containing a 5-chloro-8-quinolinol arm are most competent for 1,3-chloroamine formation. Furthermore, only the phosphoramidate cis diastereomers al...
Source: Tetrahedron - October 27, 2023 Category: Chemistry Authors: Annu Anna Thomas Frederick J Seidl Joel T Mague Shyam Sathyamoorthi Source Type: research
Ring-Opening Reactions of Phosphoramidate Heterocycles
We present protocols for the conversion of phosphoramidate heterocycles into 1,3-chloroamines and 1,3-aminoalcohols. For the formation of chloroamines, our optimized protocol involves heating the phosphoramidate starting material with 4 equivalents of HCl in a dioxane/toluene solvent mixture. The substituents on the phosphoramidate starting material have a profound influence on product formation. Phosphoramidates with a variety of aza-heterocyclic substituents engage, but those containing a 5-chloro-8-quinolinol arm are most competent for 1,3-chloroamine formation. Furthermore, only the phosphoramidate cis diastereomers al...
Source: Tetrahedron - October 27, 2023 Category: Chemistry Authors: Annu Anna Thomas Frederick J Seidl Joel T Mague Shyam Sathyamoorthi Source Type: research
Ring-Opening Reactions of Phosphoramidate Heterocycles
We present protocols for the conversion of phosphoramidate heterocycles into 1,3-chloroamines and 1,3-aminoalcohols. For the formation of chloroamines, our optimized protocol involves heating the phosphoramidate starting material with 4 equivalents of HCl in a dioxane/toluene solvent mixture. The substituents on the phosphoramidate starting material have a profound influence on product formation. Phosphoramidates with a variety of aza-heterocyclic substituents engage, but those containing a 5-chloro-8-quinolinol arm are most competent for 1,3-chloroamine formation. Furthermore, only the phosphoramidate cis diastereomers al...
Source: Tetrahedron - October 27, 2023 Category: Chemistry Authors: Annu Anna Thomas Frederick J Seidl Joel T Mague Shyam Sathyamoorthi Source Type: research
Ring-Opening Reactions of Phosphoramidate Heterocycles
We present protocols for the conversion of phosphoramidate heterocycles into 1,3-chloroamines and 1,3-aminoalcohols. For the formation of chloroamines, our optimized protocol involves heating the phosphoramidate starting material with 4 equivalents of HCl in a dioxane/toluene solvent mixture. The substituents on the phosphoramidate starting material have a profound influence on product formation. Phosphoramidates with a variety of aza-heterocyclic substituents engage, but those containing a 5-chloro-8-quinolinol arm are most competent for 1,3-chloroamine formation. Furthermore, only the phosphoramidate cis diastereomers al...
Source: Tetrahedron - October 27, 2023 Category: Chemistry Authors: Annu Anna Thomas Frederick J Seidl Joel T Mague Shyam Sathyamoorthi Source Type: research
Ring-Opening Reactions of Phosphoramidate Heterocycles
We present protocols for the conversion of phosphoramidate heterocycles into 1,3-chloroamines and 1,3-aminoalcohols. For the formation of chloroamines, our optimized protocol involves heating the phosphoramidate starting material with 4 equivalents of HCl in a dioxane/toluene solvent mixture. The substituents on the phosphoramidate starting material have a profound influence on product formation. Phosphoramidates with a variety of aza-heterocyclic substituents engage, but those containing a 5-chloro-8-quinolinol arm are most competent for 1,3-chloroamine formation. Furthermore, only the phosphoramidate cis diastereomers al...
Source: Tetrahedron - October 27, 2023 Category: Chemistry Authors: Annu Anna Thomas Frederick J Seidl Joel T Mague Shyam Sathyamoorthi Source Type: research
Ring-Opening Reactions of Phosphoramidate Heterocycles
We present protocols for the conversion of phosphoramidate heterocycles into 1,3-chloroamines and 1,3-aminoalcohols. For the formation of chloroamines, our optimized protocol involves heating the phosphoramidate starting material with 4 equivalents of HCl in a dioxane/toluene solvent mixture. The substituents on the phosphoramidate starting material have a profound influence on product formation. Phosphoramidates with a variety of aza-heterocyclic substituents engage, but those containing a 5-chloro-8-quinolinol arm are most competent for 1,3-chloroamine formation. Furthermore, only the phosphoramidate cis diastereomers al...
Source: Tetrahedron - October 27, 2023 Category: Chemistry Authors: Annu Anna Thomas Frederick J Seidl Joel T Mague Shyam Sathyamoorthi Source Type: research
Ring-Opening Reactions of Phosphoramidate Heterocycles
We present protocols for the conversion of phosphoramidate heterocycles into 1,3-chloroamines and 1,3-aminoalcohols. For the formation of chloroamines, our optimized protocol involves heating the phosphoramidate starting material with 4 equivalents of HCl in a dioxane/toluene solvent mixture. The substituents on the phosphoramidate starting material have a profound influence on product formation. Phosphoramidates with a variety of aza-heterocyclic substituents engage, but those containing a 5-chloro-8-quinolinol arm are most competent for 1,3-chloroamine formation. Furthermore, only the phosphoramidate cis diastereomers al...
Source: Tetrahedron - October 27, 2023 Category: Chemistry Authors: Annu Anna Thomas Frederick J Seidl Joel T Mague Shyam Sathyamoorthi Source Type: research
Synthesis of psychotropic alkaloids from < em > Galbulimima < /em >
Tetrahedron. 2022 Nov 5;126:133064. doi: 10.1016/j.tet.2022.133064. Epub 2022 Oct 5.ABSTRACTEfficient syntheses of valuable natural products open gateways from kind learning environments to wicked worlds, where long-term, interdisciplinary research questions can be asked and answered. In this Perspective, we discuss the Galbulimima (GB) alkaloids, metabolites of a rainforest canopy tree that exhibit potent but poorly understood effects in humans, including accounts of hallucination. Recent syntheses from our group have opened up GB alkaloid chemical space for investigation by way of new cross-coupling reactions and gram-sc...
Source: Tetrahedron - October 9, 2023 Category: Chemistry Authors: Stone Woo Eleanor M Landwehr Ryan A Shenvi Source Type: research
