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A convenient synthesis of N-boc protected primary amines via the reaction of organoboranes with Li or K t-butyl-N-tosyloxycarbamate

Jean-Pierre Genet 1 Josef Hajicek Laurent Bischoff 2 Christine Greck 3
1 SSOPN - Synthèses sélective organique et produits naturels
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
3 ILV - Institut Lavoisier de Versailles
Abstract : Primary and secondary alkylboranes reacted rapidly at low temperature with Li or K t-butyl-N-tosyloxycarbamate (LiBTOC or KBTOC) to give the corresponding N-Boc protected primary amines in modest to good yields (16–81%). N-Boc primary amines were obtained from the reaction of alkylboranes with Lithium or Potassium salts of t-butyl-N-tosyloxycarbamate.
Keywords : Amination Organoboranes t-Butyl-N-tosyloxycarbamate
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02385498
Contributor : Laurent Bischoff <>
Submitted on : Thursday, November 28, 2019 - 6:41:20 PM
Last modification on : Wednesday, October 14, 2020 - 4:10:04 AM

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COMUE-NORMANDIE | ENSCP | UVSQ | ILV | INC-CNRS | INSA-ROUEN | UNIROUEN | COBRA | INSA-GROUPE | PARISTECH | CNRS | UNILEHAVRE | ENSICAEN | UNICAEN | PSL

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Jean-Pierre Genet, Josef Hajicek, Laurent Bischoff, Christine Greck. A convenient synthesis of N-boc protected primary amines via the reaction of organoboranes with Li or K t-butyl-N-tosyloxycarbamate. Tetrahedron Letters, Elsevier, 1992, 33 (19), pp.2677-2680. ⟨10.1016/S0040-4039(00)79055-1⟩. ⟨hal-02385498⟩

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