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  • Title: Synthetically amenable amide derivatives of tosylated-amino acids as organocatalysts for enantioselective allylation of aldehydes: computational rationale for enantioselectivity.
    Author: Ghosh D, Sahu D, Saravanan S, Abdi SH, Ganguly B, Khan NU, Kureshy RI, Bajaj HC.
    Journal: Org Biomol Chem; 2013 Jun 07; 11(21):3451-60. PubMed ID: 23411590.
    Abstract:
    A phenylalanine derived chiral amide is developed that serves as an effective organocatalyst for the reaction of allyltrichlorosilane with aryl, hetero-aryl and α,β-unsaturated aldehydes to afford the desired homoallylic alcohols in good yield (up to 90%) and high enantioselectivity (up to 99%). The experimental results and DFT calculations suggest that para substituted aromatic aldehydes as substrate show higher ee in the product than their ortho/meta counterparts. The (1)H and (13)C NMR spectra study corroborated the calculated results. The chiral organocatalyst can be easily synthesized from optically pure phenylalanine in two simple steps with 90% overall yield.
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