Convenient Synthesis of 1,2-Diamines from <font>β</font>-Chloro Amines: Precursors of New Substituted Piperazin-2-ones

Slama, Soumaya; Elemine, Brahim Ould; Besbes, Rafâa

doi:10.1080/00397911.2012.700080

Cited by 5 publications

(2 citation statements)

References 26 publications

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“…The same procedure was used to convert 7b and 7c to 8b and 8c, respectively. tert-Butyl (R)-Benzyl(2-(((benzyloxy)carbonyl)amino)-4-((tertbutyldiphenylsilyl)oxy)butyl)carbamate (9). To a stirred solution of 8a (1.10 g, 1.34 mmol) in CH 3 OH (15 mL) were added Raney-Ni (0.90 g, prewashed with absolute ethanol) and 0.1 mL of acetic acid, and the stirring was continued for 14 h at rt under a hydrogen atmosphere.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…A wide range of approaches are available in the literature toward the synthesis of this ubiquitous motif. While metal-catalyzed diamination reactions − are the most common approach toward their synthesis, methods based on the functionalization of nitro alkanes, amino acids, aziridines, β-chloro amines, and aldehydes through umpolung reactions are also available. Recently, Masson and co-workers have reported an efficient method for the asymmetric synthesis of 1,2-diamines through amination of enecarbamates .…”

Section: Introductionmentioning

confidence: 99%

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Enantioselective Synthesis of 2-Aminomethyl and 3-Amino Pyrrolidines and Piperidines through 1,2-Diamination of Aldehydes

Ansari

Ramapanicker

2018

J. Org. Chem.

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An efficient method for the synthesis of 1,2-diamines from aldehydes through proline-catalyzed asymmetric α-amination followed by reductive amination is reported. The products resemble those obtained through direct asymmetric diamination of terminal alkenes. The methodology is used to synthesize 2-aminomethyl and 3-amino pyrrolidines and piperidines in high yields and with a good enantioselectivity. The usefulness of the method is demonstrated through the synthesis of a 2-aminomethyl iminocyclitol.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enantioselective Synthesis of 2-Aminomethyl and 3-Amino Pyrrolidines and Piperidines through 1,2-Diamination of Aldehydes

Ansari

Ramapanicker

2018

J. Org. Chem.

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ChemInform Abstract: Convenient Synthesis of 1,2‐Diamines from β‐Chloro Amines: Precursors of New Substituted Piperazin‐2‐ones.

2013

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Diastereoselective Synthesis and Configurational Assignment of Novel Functionalized Cyclic Sulfamidites Precursors of Cyclic Sulfamidates

Slama

Arfaoui

Besbes

2016

Heteroatom Chemistry

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New 3,4,5‐trisubstituted sulfamidites were prepared through cyclization of β‐amino alcohol diesters with thionyl chloride. The oxidation of these N‐alkylated sulfamidites into the corresponding sulfamidates was then performed. Interestingly, the NMR spectra of the prepared sulfamidites revealed that the ratios of the exo and endo diastereomers of these compounds were influenced by the substituents on the α‐carbon. In addition, theoretical calculations at the DFT B3LYP/6‐31G(d) level were carried and indicated that the exo‐diastereomers were more stable than the endo forms.

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Convenient Synthesis of 1,2-Diamines from β-Chloro Amines: Precursors of New Substituted Piperazin-2-ones

Cited by 5 publications

References 26 publications

Enantioselective Synthesis of 2-Aminomethyl and 3-Amino Pyrrolidines and Piperidines through 1,2-Diamination of Aldehydes

Enantioselective Synthesis of 2-Aminomethyl and 3-Amino Pyrrolidines and Piperidines through 1,2-Diamination of Aldehydes

ChemInform Abstract: Convenient Synthesis of 1,2‐Diamines from β‐Chloro Amines: Precursors of New Substituted Piperazin‐2‐ones.

Diastereoselective Synthesis and Configurational Assignment of Novel Functionalized Cyclic Sulfamidites Precursors of Cyclic Sulfamidates

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