𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Electrophilic amination: first direct transfer of NHBoc with Li t-butyl-n-tosyloxycarbamate.

✍ Scribed by J.P. Genet; S. Mallart; C. Greck; E. Piveteau

Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
238 KB
Volume
32
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

rue P. et M. Curie -7523 1 Paris cedex 05 (Prance)

,4bstra& Lithium t-butyl-N-tosyloxycarbamate (LiBTOC) has been found to be an electrophilic aminating reagent. This species reacts with organometallic reagents, ester etwlates and a-cuprophosphonates to provide primary amines as well as a-amitwcarboxylic and phosphor& esters in their N-(Boc) protected form. (35-80 % isolated yields).

πŸ“œ SIMILAR VOLUMES

Asymmetric synthesis of Ξ±-amino acid der
Asymmetric synthesis of Ξ±-amino acid derivatives via an electrophilic amination of chiral amide cuprates with Li t-butyl-N-tosyloxycarbamate
✍ Nan Zheng; Joseph D. Armstrong III; J.Christopher McWilliams; R.P. Volante πŸ“‚ Article πŸ“… 1997 πŸ› Elsevier Science 🌐 French βš– 218 KB

The utility of lithium t-butyl-N-tosyloxycarbamate (LiBTOC) as a ( + )NHBOC synthon in highly diastereoselective reactions with chiral cis-aminoindanol derived amide cuprates is described. The diastereoselectivities of these reactions ranged from 96% to greater than 99%. The subsequent transformatio

Reaction of polyfluorinated imines with
Reaction of polyfluorinated imines with trifluoromethyltrimethylsilane. Direct synthesis of N-(perfluoro-t-butyl)amines
✍ Viacheslav A. Petrov πŸ“‚ Article πŸ“… 2000 πŸ› Elsevier Science 🌐 French βš– 143 KB

The reaction of N-arylimines of hexaΒ―uoroacetone and CF 3 Si(CH 3 ) 3 (1) in the presence of CsF results in a 48Β±84% yield formation of ArN(H)C(CF 3 ) 3 . The reaction requires an equimolar amount of CsF and rapidly proceeds in solvents such as THF or monoglyme. Interaction of CF 3 NC(CF 3 ) 2 with