title: Asymmetric Garratt-Braverman cyclization: a route to axially chiral aryl naphthalene-amino acid hybrids.
abstract: We report the first example of a highly diastereoselective Garratt-Braverman cyclization leading to the synthesis of chiral aryl naphthalene-amino acid hybrids in excellent yields. The stereogenecity in the amino acid has induced high diastereoselectivity for the reaction. Computations based on density functional theory indicated a lower activation free energy barrier for the M isomer as compared to that for the P diastereomer (ΔΔG = 3.48 kcal/mol). Comparison of the recorded CD spectrum of the product with the calculated one also supported the preferential formation of the M diastereomer.
authors.affiliation: Department of Chemistry, Indian Institute of Technology , Kharagpur 721 302, India.
authors.forename: Tapobrata
authors.initials: T
authors.lastname: Mitra
authors.forename: Saibal
authors.initials: S
authors.lastname: Jana
authors.forename: Sharmila
authors.initials: S
authors.lastname: Pandey
authors.forename: Prabuddha
authors.initials: P
authors.lastname: Bhattacharya
authors.forename: Uttam K
authors.initials: UK
authors.lastname: Khamrai
authors.forename: Anakuthil
authors.initials: A
authors.lastname: Anoop
authors.forename: Amit
authors.initials: A
authors.lastname: Basak