Nucleophilic Ring Opening of Cyclic 1,2-Sulfites with Nitrogen Nucleophiles. A Route to Enantiopure Benzylic Amino Alcohols.

Nymann, Kirsten; Mylvaganam, Saravanapavan; Svendsen, John S.; Laskar, Inamur Rahaman; Chaudhuri, Nirmalendu Ray; Ranta, Kirsi; Rojo, Teófilo

doi:10.3891/acta.chem.scand.52-1060

Cited by 7 publications

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“…Starting from ( S )-phenylglycinol 6 , the second approach to orthogonally protected diamine 10 is depicted in Scheme . ( S )-Phenylglycinol was converted to its N -nosylated derivative 7 by exposure to NsCl in the presence of TEA . The N -nosylated amino alcohol 7 was activated by reaction with MsCl/TEA to afford the corresponding mesylate 8 .…”

Section: Discussionmentioning

confidence: 99%

Synthesis of Enantiomerically Pure 5-Substituted Piperazine-2-Acetic Acid Esters as Intermediates for Library Production

et al. 2019

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The piperazine heterocycle is housed within a large number of FDA-approved drugs and biological probe compounds. Structurally, however, these compounds are mostly confined to substitutions on the two ring nitrogen atoms, rationalizing the expansion of piperazine chemical diversity through carbon substitutions. On the basis of the concept of systematic chemical diversity, a divergent six-step synthesis was developed in which chiral amino acids were transformed, with high diastereoselectivity, into either cis or trans 5-substituted piperazine-2-acetic acid esters that could be chromatographically rendered diastereomerically homogeneous. Starting from six commercially available amino acids or their respective amino alcohols (both antipodes), we obtained a complete set of 24 protected chiral 2,5-disubstituted piperazines, as single stereoisomers in multigram quantities. These diverse and versatile piperazines can be functionalized on either nitrogen atom, allowing them to be used as starting materials for parallel library synthesis and as intermediates for the targeted production of more complex C-substituted piperazine compounds.

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Section: Discussionmentioning

confidence: 99%