245735-57-3Relevant academic research and scientific papers
Asymmetric synthesis of α- And β-amino acids by diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl) imines
Almansa, Raquel,Collados, Juan F.,Guijarro, David,Yus, Miguel
experimental part, p. 1421 - 1431 (2010/11/02)
The diastereoselective addition of triorganozincates to (R)-N-(tert-butanesulfinyl)imines has been used as a key step to achieve the synthesis of highly enantiomerically enriched N-protected α- and β-amino acids. Desulfinylation of the addition products followed by benzoylation of the nitrogen atom of the obtained primary amines and oxidation of one of the substituents on the carbon atom connected to the nitrogen complete the sequence. Using the same configuration in the sulfinyl chiral auxiliary, α-amino acids with the (R) or the (S) configuration can be prepared by choosing the proper combination of imine and organozincate. α,α- Disubstituted α-amino esters with high enantiomeric purity can also be prepared when α-imino esters are the starting substrates.
Asymmetric synthesis of δ-substituted α,β-unsaturated δ-lactams by ring closing metathesis of enantiomerically pure N-acryloyl-homoallylic amines
Fiorelli, Claudio,Savoia, Diego
, p. 6022 - 6028 (2008/02/10)
(Chemical Equation Presented) Optically pure secondary homoallylic amines, obtained by highly diastereoselective addition of allylmetal reagents to imines derived from chiral amines, were N-dealkylated, and the primary amines were converted to N-acryloyl
Enantioselective Synthesis of Chiral Homoallyl Alcohols and Homoallylamines by Nucleophilic Addition of an Allylboron Reagent Modified by a Polymer-Supported Chiral Ligand
Itsuno, Shinichi,Watanabe, Katsuhiro,El-Shehawy, Ashraf A.
, p. 89 - 94 (2007/10/03)
Crosslinked polymer-supported chiral N-sulfonylamino alcohols 5-8 have been prepared by suspension polymerization of enantiopure N-sulfonylamino alcohol monomers 1-4 with styrene and divinylbenzene. Polymer-supported chiral allylboron reagents were prepared from the polymeric chiral ligands. Enantioselective additions of the polymer-supported allylboron reagents to aldehydes and N-(trimethylsilyl)imines have been successfully carried out in the heterogeneous system. The corresponding optically active homoallyl alcohols and homoallylamines were obtained in high yields with high enantioselectivities (up to 95% ee) which are almost the same as those obtained from homogeneous analogues. The polymer-supported chiral ligands used were recovered easily and can be reused without any loss of activity.
