945544-18-3Relevant academic research and scientific papers
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 (2007)
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.
Role of the countercation in diastereoselective alkylations of pyramidalized bicyclic serine enolates. An easy approach to α-benzylserine
Jimenez-Oses, Gonzalo,Aydillo, Carlos,Busto, Jesus H.,Zurbano, Maria M.,Peregrina, Jesus M.,Avenoza, Alberto
, p. 5399 - 5402 (2007)
(Chemical Equation Presented) The use of a chiral serine equivalent as an excellent chiral building block has been demonstrated in the synthesis of α-benzylserine through a diastereoselective lithium enolate alkylation reaction and subsequent acid hydroly
