365441-87-8Relevant articles and documents
A strategy for generating alkyl radicals from aliphatic esters and lactones via sequential hydrolysis and photoinduced decarboxylation
Saito, Hikaru,Kanetake, Takayuki,Osaka, Kazuyuki,Maeda, Kousuke,Morita, Toshio,Yoshimi, Yasuharu
supporting information, p. 1645 - 1648 (2015/03/14)
Sequential hydrolysis and photoinduced decarboxylation of methyl aliphatic esters lead to efficient generation of alkyl radicals under mild conditions. The generated alkyl radicals react with a variety of reagents to produce addition, reduction, and substitution products. In addition, the new tin and halogen free process for alkyl radical generation is applicable to a variety of aliphatic esters including those of dipeptides, steroids, saccharides, and lactones.
Ligand-controlled α- And β-arylation of acyclic N-boc amines
Millet, Anthony,Dailler, David,Larini, Paolo,Baudoin, Olivier
supporting information, p. 2678 - 2682 (2014/03/21)
The palladium-catalyzed ligand-controlled arylation of α-zincated acyclic amines, obtained by directed α-lithiation and transmetalation, is described. Whereas PtBu3 gave rise to α-arylated Boc-protected amines, more flexible N-phenylazole-based phosphine ligands induced major β-arylation through migrative cross-coupling. All manner of control: The arylation of α-zincated acyclic Boc-protected amines was selectively performed at the α- or β-position in a ligand-controlled manner. α-Arylation occurs by direct reductive elimination of the α-palladated intermediate whereas β-arylation involves palladium migration along the alkyl chain. Boc=tert-butoxycarbonyl.
Decarboxylative reduction of free aliphatic carboxylic acids by photogenerated cation radical
Yoshimi, Yasuharu,Itou, Tatsuya,Hatanaka, Minoru
, p. 5244 - 5246 (2008/09/19)
The decarboxylation of free carboxylic acids was effected by a photogenerated cation radical of phenanthrene to yield the reduction product in the presence of a thiol, which provides an alternative method to the Barton decarboxylation procedure for aliphatic acids such as N-Boc amino acids. The Royal Society of Chemistry.
Boc-protected amines via a mild and efficient one-pot curtius rearrangement
Lebel, Helene,Leogane, Olivier
, p. 4107 - 4110 (2007/10/03)
(Chemical Equation Presented) The reaction of a carboxylic acid with di-tert-butyl dicarbonate and sodium azide allowed the formation of an acyl azide intermediate, which undergoes a Curtius rearrangement in the presence of tetrabutylammonium bromide and zinc(II) triflate. The trapping of the isocyanate derivative in the reaction mixture led to the desired tert-butyl carbamate in high yields at low temperature. These reaction conditions are compatible with a variety of substrates, including malonate derivatives, which provide access to protected amino acids.
An expedient transformation of alcohols into N-Boc-amines
Sliwinska,Zwierzak
, p. 2127 - 2130 (2007/10/03)
t-Butyl methyl iminodicarbonate (3) can be easily alkylated with primary or secondary alcohols under Mitsunobu conditions (DIAD, TPP) to give the corresponding N-alkyl iminodicarbonates. Partial deprotection of the latter with methanolic potassium hydroxi
Reductive BOC-amination of aldehydes
Bernacka, Elbieta,Klepacz, Anna,Zwierzak, Andrzej
, p. 5093 - 5094 (2007/10/03)
Base-assisted elimination-reduction of α-amidoalkyl sulfones with sodium borohydride proceeds in tetrahydrofuran at room temperature leading to the corresponding BOC-amines in good yields.