Mild Electrochemical Deprotection of N‐Phenylsulfonyl N‐Substituted Amines Derived from (R)‐Phenylglycinol

Abstract

The electrochemical reduction of N‐phenylsulfonyl N‐substituted amines in a protic medium under constant cathodic potential was found to be a mild desulfonylation method, which is able to challenge the chemical ones. The influence of the nature of the N‐substituents was considered in order to clarify the mechanistic aspects and to evaluate the scope of the method.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

Oxaziridine-mediated enantioselective aminohydroxylation of styrenes catalyzed by copper(II) bis(oxazoline) complexes

“…( R ) -N -Benzenesulfonyl-2-amino-2-phenylethanol was prepared from ( R )-phenylglycinol using a procedure described by Quintard and coworkers 12. Spectral data were in agreement with previously reported values 8a.…”

Ring-opening, cycloaddition and rearrangement reactions of nitrogen-substituted cyclopropane derivatives

“…140 Indeed, the related partial conversion of N-benzyl-N-cyclopropyl phenylsulfonamide into a ring-opened product, N-benzyl-N-propylamine, upon reductive desulfonation performed electrochemically, is proposed to proceed via the formation of an Ncyclopropylaminyl radical. 142,143 Using lithium aluminium hydride as the metallating agent, the imine function generated is reduced and the final product is an amine. 60 Examples are displayed in Scheme 46.…”

Synthesis of 1,2‐Amino Alcohols by Sigmatropic Rearrangements of 3‐(N‐Tosylamino)allylic Alcohol Derivatives

“…[18] To investigate the feasibility of sigmatropic rearrangements involving derivatives B or D, acyclic 3-(N-tosylamino)allylic alcohols (EWG = Ts) were selected as substrates. Though sulfonamides are less readily cleaved than some other nitrogen protecting groups, [19] they offer the advantage of being…”