147169-48-0Relevant articles and documents
Highly Enantiospecific Borylation for Chiral α-Amino Tertiary Boronic Esters
Qi, Qingqing,Yang, Xuena,Fu, Xiaoping,Xu, Shiqing,Negishi, Ei-ichi
supporting information, p. 15138 - 15142 (2018/10/26)
Herein we report a highly efficient and enantiospecific borylation method to synthesize a wide range of enantiopure (>99 % ee) α-amino tertiary boronic esters. The configurationally stable α-N-Boc substituted tertiary organolithium species and pinacolborane (HBpin) underwent enantiospecific borylation at ?78 °C with the formation of a new stereogenic C?B bond. This reaction has a broad scope, enabling the synthesis of various α-amino tertiary boronic esters in excellent yields and, importantly, with universally excellent enantiospecificity (>99 % es) and complete retention of configuration.
Sustainable and chemoselective N-Boc protection of amines in biodegradable deep eutectic solvent
Azizi, Najmedin,Shirdel, Fatemeh
, p. 1069 - 1074 (2017/05/12)
Abstract: A green and practical approach for the chemoselective N-tert-butyloxycarbonylation of structurally diverse amines with di-tert-butyl dicarbonate (Boc2O) is described. Selective N-Boc protection was achieved in excellent yields in urea-choline chloride deep eutectic solvent (DES) as the most promising environmentally benign and cost-effective solvent under mild reaction condition. DES can protect various aromatic and aliphatic amines using Boc2O in good to excellent yields in short reaction times without any side products. Graphical abstract: [Figure not available: see fulltext.].
Synthesis of N-Boc-Propargylic and Allylic Amines by Reaction of Organomagnesium Reagents with N-Boc-Aminals and Their Oxidation to N-Boc-Ketimines
Kano, Taichi,Kobayashi, Ryohei,Maruoka, Keiji
supporting information, p. 276 - 279 (2016/02/03)
Previously inaccessible N-Boc-protected propargylic and allylic amines were synthesized by the reaction between N-Boc-aminals and organomagnesium reagents through the in situ generated N-Boc-imine intermediates. The obtained N-Boc-propargylic amines could be readily converted into unprecedented N-Boc-ketimines by oxidation with manganese dioxide.