Versatile Synthesis of Free and N‐Benzyloxycarbonyl‐Protected 2,2‐Disubstituted Taurines

Abstract

An effective and versatile method was developed to synthesize N‐benzyloxycarbonyl‐protected and free 2,2‐disubstituted taurines. Several novel 2,2‐disubstituted taurines, including aliphatic/aromatic and cyclic/acyclic derivatives, were obtained, which demonstrates the generality of this method. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

An efficient and facile synthesis of N-Cbz-β-aminoalkanesulfonamides

“…Our group modified the method to avoid the formation of the Michael adduct. In our procedure, DEAD and triphenylphosphine were mixed first to form a white precipitate of the active intermediate, the adduct of DEAD and triphenylphosphine, and subsequently a solution of an N-Cbz-amino alcohol and thiolacetic acid was added slowly into the reaction mixture [35,36]. Following our modified procedure, a series of thiolacetates 2ag were prepared in satisfactory to good yields from 42% to 82% (Table 1).…”

Synthesis of N‐Vinyloxazolidinones and Morpholines from Amino Alcohols and Vinylsulfonium Salts: Analysis of the Outcome's Dependence on the N‐Protecting Group by Nanospray Mass Spectrometry

“…The spectroscopic data are consistent with those reported. [17] Benzyl 1-Hydroxy-2-methylpropan-2-ylcarbamate (3j): [18] 24.0 (CH 3 ) ppm. The spectroscopic data are consistent with those reported.…”

“…The spectroscopic data are consistent with those reported. [18] Benzyl 2-Hydroxyethylcarbamate (3k): [19] Following general procedure A. Yield 68 %; white solid.…”

A Short Access to Symmetrically α,α-Disubstituted α-Amino Acids from Acyl Cyanohydrins

“…Classical routes involve modification of ketones already displaying the R substituents by Bucherer-Bergs, 7 Strecker, 8 or Ugi 9 reactions, followed by amine deprotection and/or hydrolysis (Scheme 1, routes 1 and 2). Alternatively, the R moiety is introduced from electrophilic sources (organic halides or Michael acceptors), by reaction with nitroacetates, isocyanoacetates, glycine-derived imines or azlactones 10 (route 3).…”