112302-87-1Relevant academic research and scientific papers
Palladium-catalyzed β-arylation of silyl ketene acetals and application to the synthesis of benzo-fused δ-lactones
Aspin, Sam,Lopez-Suarez, Laura,Larini, Paolo,Goutierre, Anne-Sophie,Jazzar, Rodolphe,Baudoin, Olivier
supporting information, p. 5056 - 5059 (2013/10/22)
Silyl ketene acetals are shown to be competent nucleophiles in Pd-catalyzed migrative C(sp3)-H arylations. Compared to the parent ester lithium enolates, they possess decreased reactivity but enhanced chemoselectivity. This behavior was exploited through the synthesis of valuable benzo-fused δ-lactones such as 1-isochromanones and dihydrocoumarins.
Synthesis of aromatic α-aminoesters: Palladium-catalyzed long-range arylation of primary Csp3-H bonds
Aspin, Sam,Goutierre, Anne-Sophie,Larini, Paolo,Jazzar, Rodolphe,Baudoin, Olivier
supporting information, p. 10808 - 10811 (2013/01/15)
Remote control: The title reaction for β-Iζ arylation of α-amino esters with aryl bromides is described. This reaction, which occurs selectively at the terminal position of linear alkyl chains, gives rise to synthetically useful (hetero)arylalanines and homologues after debenzylation (see scheme). Copyright
Copper-catalyzed amination of ketene silyl acetals with hydroxylamines: Electrophilic amination approach to α-amino acids
Matsuda, Naoki,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
supporting information, p. 11827 - 11831 (2013/01/15)
Role reversal: The title reaction has been developed to deliver α-amino acids under very mild reaction conditions (see scheme; dpppen=1,5-bis(diphenylphosphino)pentane). The catalysis provides a new C-N bond-forming approach for the synthesis of α-amino a
Double nucleophilic N-alkylation of α-oxime-esters with Grignard reagents
Mizutani, Yusuke,Tanimoto, Hiroki,Morimoto, Tsumoru,Nishiyama, Yasuhiro,Kakiuchi, Kiyomi
supporting information, p. 5903 - 5906,4 (2020/08/20)
Double nucleophilic N-alkylation of α-oxime-esters, affording N,N-dialkyl-α-amino acids is herein described. Grignard reagents accomplished double N-alkylations via umpolung and various N,N-dialkylated α-amino acids were successfully synthesized in 15 min. Both electron-withdrawing sulfonyl groups and electron-donating silyl and methyl groups on oximes were available. Alkylmagnesium species and (E)-configuration of α-oxime-ester were essential to this cascade reaction.
Highly enantioselective access to α-dibenzylamino ketones from chiral nonracemic α-bromo α′-sulfinyl ketones by dynamic kinetic resolution: Synthesis of (2R,1′S)-2-[1-(dibenzylamino)alkyl]oxiranes
Geant, Pierre-Yves,Martinez, Jean,Salom-Roig, Xavier J.
experimental part, p. 1300 - 1309 (2011/04/17)
A novel and efficient synthesis of enantiomerically pure α-dibenzylamino α′-sulfinyl ketones starting from a mixture of both epimers of α-bromo α′-(R)-sulfinyl ketone has been realized through combined in situ substitution-epimerization in a so-called Dynamic Kinetic Resolution (DKR). The scope of the reaction has been examined, and four differently substituted α-(S)-dibenzylamino α′-(R)- sulfinyl ketones were obtained in good yields with excellent diastereoselectivities. The utility of these derivatives was further illustrated with a highly stereoselective synthesis of syn-(2R,1′S)-2-(1- dibenzylaminoalkyl)oxiranes.
DIBENZYLAMINOACETATES AS USEFUL SYNTHETIC EQUIVALENTS OF GLYCINE IN THEi SYNTHESIS OF α-AMINO-β-HYDROXYACIDS
Guanti, Giuseppe,Banfi, Luca,Narisano, Enrica,Scolastico, Carlo
, p. 3671 - 3684 (2007/10/02)
The stereochemical course of three new simple methodologies for the preparation of α-amino-β-hydroxyacids starting from dibenzylaminoacetates as synthetic equivalents of glycine is described.While the aldol-type condensation via lithium enolates gave results highly dependent on the aldehyde employed, producing in some cases diastereoselectivities up to 5:1 for the anti isomers, the acid-catalysed aldol condensation of silyl ketene acetals yielded predominantly syn adducts with selectivities from 5:1 to 32:1.Finally the acylation-reduction procedure gave the best results in terms of yields and stereoselectivities, affording syn isomers with excellent induction ( 13:1).
Alkylation and Condensation Reactions of N,N-Dibenzylglycine Esters: Synthesis of α-Amino Acid Derivatives
Gray, Brian D.,Jeffs, Peter W.
, p. 1329 - 1330 (2007/10/02)
Upon deprotonation N,N-dibenzylglycine esters undergo alkylation and condensation reactions at the α-carbon atom with various electrophiles.
