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  • Title: Theoretical evidence for pyramidalized bicyclic serine enolates in highly diastereoselective alkylations.
    Author: Aydillo C, Jiménez-Osés G, Busto JH, Peregrina JM, Zurbano MM, Avenoza A.
    Journal: Chemistry; 2007; 13(17):4840-8. PubMed ID: 17366514.
    Abstract:
    A new chiral serine equivalent and its enantiomer have been synthesized from (S)- and (R)-N-Boc-serine methyl esters (Boc: tert-butyloxycarbonyl). The use of these compounds as chiral building blocks has been demonstrated in the synthesis of alpha-alkyl alpha-amino acids by diastereoselective potassium enolate alkylation reactions and subsequent acid hydrolyses. Theoretical studies were performed to elucidate 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.
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