1204391-07-0Relevant articles and documents
N-Boc-aminals as easily accessible precursors for less accessible N-Boc-imines: Facile synthesis of optically active propargylamine derivatives using Mannich-type reactions
Yurino, Taiga,Aota, Yusuke,Asakawa, Daisuke,Kano, Taichi,Maruoka, Keiji
, p. 3687 - 3700 (2016/06/06)
We developed a facile and practical synthesis of N-Boc-aminals, which can be used as precursors for less accessible N-Boc-imines. Aminals were obtained via simple dehydration condensation reactions of t-butyl carbamate (BocNH2) and various aldehydes in acetic anhydride, followed by filtration and washing with hexane. The obtained N-Boc-alkynylaminals could be successfully applied in enantioselective Mannich-type reactions, catalyzed by chiral phosphoric acids, to afford optically active propargylamine derivatives.
Br?nsted acid-catalyzed Mannich reaction through dual activation of aldehydes and N-Boc-imines
Kano, Taichi,Aota, Yusuke,Asakawa, Daisuke,Maruoka, Keiji
supporting information, p. 16472 - 16474 (2015/11/18)
In the presence of a Br?nsted acid catalyst, both aldehydes and N-Boc-aminals were converted to enecarbamates and N-Boc-iminium salts as activated nucleophiles and electrophiles, respectively, giving unprecedented Mannich adducts. The asymmetric variant of the present Mannich reaction has also been demonstrated with a chiral phosphoric acid catalyst.
Trimethylchlorosilane-promoted aza-Mannich reaction of enecarbamates and aldimines
Wu, Pengcheng,Lin, Deqin,Lu, Xiaoxia,Zhou, Li,Sun, Jian
experimental part, p. 7249 - 7251 (2010/02/28)
A trimethylchlorosilane-promoted aza-Mannich reaction is reported utilizing enecarbamates as the nucleophile and aromatic N-Boc aldimines as the electrophile. A variety of nucleophiles and electrophiles are tolerated by the reaction conditions, delivering