134899-85-7Relevant academic research and scientific papers
Enantioselective Synthesis of α-Substituted Serine Derivatives via Cu-Catalyzed Oxidative Desymmetrization of 2-Amino-1,3-diols
Yamamoto, Kosuke,Ishimaru, Shota,Oyama, Tatsuya,Tanigawa, Satoko,Kuriyama, Masami,Onomura, Osamu
, p. 660 - 666 (2019/03/26)
The enantioselective copper-catalyzed oxidative desymmetrization for the synthesis of chiral α-substituted serine derivatives is reported. The combination of Cu(OTf)2/(R,R)-PhBOX catalyst system, N-bromosuccinimide, and MeOH enables us to provide chiral α-substituted serines from N-2-methylbenzoyl-protected 2-amino-1,3-diols through a simple procedure at room temperature under an air atmosphere. A variety of α-substituent including aryl and heteroaryl groups were tolerated in this method, and the corresponding chiral serine derivatives were obtained in good to high yields with high enantioselectivities.
Theoretical evidence for pyramidalized bicyclic serine enolates in highly diastereoselective alkylations
Aydillo, Carlos,Jimenez-Oses, Gonzalo,Busto, Jesus H.,Peregrina, Jesus M.,Zurbano, Maria M.,Avenoza, Alberto
, p. 4840 - 4848 (2008/02/04)
A new chiral serine equivalent and its enantiomer have been synthesized from (S)- and (R)-N-Bocserine methyl esters (Boc: tert-butyloxy-carbonyl). The use of these compounds as chiral building blocks has been demonstrated in the synthesis of α-alkyl α-amino acids by diastereoselective po tassium enolate alkylation reactions and subsequent acid hydrolyses. Theoretical studies were performed to eluci date the stereochemical outcome of both the formation of five-membered cyclic N,O-acetals and the subsequent alkylation process, which occurs with total retention of configuration. This feature could be explained in terms of the high degree of pyramidalization of enolate intermediates.
Asymmetric Syntheses via Heterocyclic Intermediates, XI Enantioselective Synthesis of (R)-(-)-α-Methylserine
Groth, Ulrich,Chiang, Yao-chung,Schoellkopf, Ulrich
, p. 1756 - 1757 (2007/10/02)
Die Titelverbindung 7 wurde in enantiomerenreiner Form durch asymmetrische Synthese dargestellt unter Verwendung des Bislyctimethers 1 von cyclo-(L-Val-DL-Ala) als Ausgangsverbindung.
