- Organocatalytic asymmetric mannich reactions with JV-Boc and JV-Cbz protected α-amido sulfones (Boc: Tert-butoxycarbonyl, Cbz: Benzyloxycarbonyl)
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Different malonates and βketoesters can react with N-tert-butoxycarbonyl- (N-Boc) and N-benzyloxycarbonyl- (N-Cbz) protected α-amido sulfones in an organocatalytic asymmetric Mannich-type reaction. The reaction makes use of a simple and easily obtained ph
- Marianacci, Olindo,Micheletti, Gabriele,Bernardi, Luca,Fini, Francesco,Fochi, Mariafrancesca,Pettersen, Daniel,Sgarzani, Valentina,Ricci, Alfredo
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p. 8338 - 8351
(2008/04/01)
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- Wolff rearrangement of Nα-Boc-/Z-protected aminodiazoketones to the corresponding β-amino acids under microwave irradiation
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The Wolff rearrangement of Nα-Boc-/Z-protected aminodiazoketones in the presence of silver benzoate under microwave irradiation is described. The reaction is found to be rapid, efficient and complete. It results in the isolation of Boc-/Z- prot
- Kantharaju,Patil, Basanagoud S.,Suresh Babu, Vommina V.
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p. 2611 - 2613
(2007/10/03)
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- Synthesis of optically active β-amino acid N-carboxyanhydrides
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(Equation presented) Methodology has been developed for the general synthesis of optically active β-amino acid N-carboxyanhydrides (β-NCAs) through cyclization of Nβ-Boc or Nβ-Cbz β-amino acids using phosphorus tribromide. The format
- Cheng, Jianjun,Ziller, Joseph W.,Deming, Timothy J.
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p. 1943 - 1946
(2007/10/03)
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- A general method for the synthesis of enantiomerically pure β- substituted, β-amino acids through α-substituted succinic acid derivatives
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A general procedure for the synthesis of enantiopure β-substituted, β- amino acids is presented. Alkylation of the sodium enolates derived from chiral N-acyloxazolidinone imides 2 (R = Me, i-Pr, t-Bu, Ph, Bn) with tert- butyl bromoacetate afforded the 2-substituted succinate derivatives 3 in good yields (82-89%) and with high selectivity (≥ 93;7). Following hydrolysis, Curtius rearrangement of the resulting carboxylic acid provided the enantiopure benzyloxycarbonyl (Cbz)-protected β-amino esters 6 in good yields (74-79%).
- Evans, David A.,Wu, Leester D.,Wiener, John J. M.,Johnson, Jeffrey S.,Ripin, David H. B.,Tedrow, Jason S.
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p. 6411 - 6417
(2007/10/03)
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