title: Synthetically amenable amide derivatives of tosylated-amino acids as organocatalysts for enantioselective allylation of aldehydes: computational rationale for enantioselectivity.
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.
authors: Discipline of Inorganic Materials and Catalysis, CSIR, Central Salt and Marine Chemicals Research Institute, G. B. Marg, Bhavnagar 364 021, Gujarat, India.
authors: Debashis
authors: D
authors: Ghosh
authors: Debashis
authors: D
authors: Sahu
authors: S
authors: S
authors: Saravanan
authors: Sayed H R
authors: SH
authors: Abdi
authors: Bishwajit
authors: B
authors: Ganguly
authors: Noor-ul H
authors: NU
authors: Khan
authors: Rukhsana I
authors: RI
authors: Kureshy
authors: Hari C
authors: HC
authors: Bajaj
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D003198:Computer Simulation; D015394:Molecular Structure; D009930:Organic Chemicals / Q000737:chemistry; D013237:Stereoisomerism; D014105:Tosyl Compounds / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000577:Amides; D000596:Amino Acids; D009930:Organic Chemicals; D014105:Tosyl Compounds