Synthesis of unnatural α-amino esters using ethyl nitroacetate and condensation or cycloaddition reactions

• Glwadys Gagnot,
• Vincent Hervin,
• Eloi P. Coutant,
• Sarah Desmons,
• Racha Baatallah,
• Victor Monnot and
• Yves L. Janin

Beilstein J. Org. Chem. 2018, 14, 2846–2852, doi:10.3762/bjoc.14.263

• benzoate, a well-known side product in this reaction [7][8]. From the aryl acetals 5g–l featuring electron-withdrawing groups, low to non-detectable amounts of the condensations products 2g–l were observed by 1H NMR analysis, and this was reflected in the isolated yield of the corresponding α-nitroesters

Cupreines and cupreidines: an established class of bifunctional cinchona organocatalysts

• Laura A. Bryant,
• Rossana Fanelli and
• Alexander J. A. Cobb

Beilstein J. Org. Chem. 2016, 12, 429–443, doi:10.3762/bjoc.12.46

• nitroolefins, and (b) Lin’s similar process with α-nitroesters using the symmetric hydrocupreidine system HCPD-44. A diastereodivergent sulfa-Michael addition developed by Melchiorre and co-workers. Melchiorre’s vinylogous Michael addition. Simpkins’s TKP conjugate addition reactions. Hydrocupreine catalyst

Organocatalytic and enantioselective Michael reaction between α-nitroesters and nitroalkenes. Syn/anti-selectivity control using catalysts with the same absolute backbone chirality

• Jose I. Martínez,
• Uxue Uria,
• Maria Muñiz,
• Efraím Reyes,
• Luisa Carrillo and
• Jose L. Vicario

Beilstein J. Org. Chem. 2015, 11, 2577–2583, doi:10.3762/bjoc.11.277

• Jose I. Martinez Uxue Uria Maria Muniz Efraim Reyes Luisa Carrillo Jose L. Vicario Department of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain 10.3762/bjoc.11.277 Abstract The asymmetric and catalytic Michael reaction between α-nitroesters and

• all cases. Keywords: asymmetric diastereodivergent; enantioselective; Michael addition; nitroalkenes; nitroesters; organocatalysis; squaramides; Introduction The absolute stereochemistry of a molecule has a paramount influence on the properties that this compound will have when interacting with

• ethyl 2-nitropropanoate and β-nitrostyrene as model substrates. Proposed models to explain the stereochemical outcome of the reaction. Enantio- and diastereoselective Michael reaction between nitroesters 1 and nitroalkenes 2 catalysed by 4.a Enantio- and diastereoselective Michael reaction between