title: Highly enantioselective synthesis of chiral allenes by sequential creation of stereogenic center and chirality transfer in a single pot operation.
abstract: Chiral allenes are readily accessed in a single pot operation in the reaction of terminal alkynes, aldehydes, chiral secondary amines, and zinc halides in good yields (up to 77% yield) and excellent enantioselectivities (up to 99% ee) in toluene at 120 °C. The reaction proceeds through initial formation of chiral propargylamine intermediates with creation of a new stereogenic center and subsequent chirality transfer via an intramolecular hydride shift to produce chiral allenes with high enantiomeric purities.
authors.affiliation: School of Chemistry, University of Hyderabad, Central University P. O., Hyderabad - 500 046, India. mpsc@uohyd.ernet.in
authors.forename: Mariappan
authors.initials: M
authors.lastname: Periasamy
authors.forename: Nalluri
authors.initials: N
authors.lastname: Sanjeevakumar
authors.forename: Manasi
authors.initials: M
authors.lastname: Dalai
authors.forename: Ramani
authors.initials: R
authors.lastname: Gurubrahamam
authors.forename: Polimera Obula
authors.initials: PO
authors.lastname: Reddy