Synthetically amenable amide derivatives of tosylated-amino acids as organocatalysts for enantioselective allylation of aldehydes: Computational rationale for enantioselectivity

Debashis Ghosh, Debashis Sahu, S. Saravanan, Sayed H.R. Abdi, Bishwajit Ganguly, Noor Ul H. Khan, Rukhsana I. Kureshy, Hari C. Bajaj

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

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 1H and 13C 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.

Original languageEnglish
Pages (from-to)3451-3460
Number of pages10
JournalOrganic and Biomolecular Chemistry
Volume11
Issue number21
DOIs
Publication statusPublished - Jun 7 2013
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Synthetically amenable amide derivatives of tosylated-amino acids as organocatalysts for enantioselective allylation of aldehydes: Computational rationale for enantioselectivity'. Together they form a unique fingerprint.

Cite this