title: Diastereoselectivity in the Staudinger reaction of pentafluorosulfanylaldimines and ketimines.
abstract: β-Lactams were diastereoselectively formed by the reaction of SF5-containing aldimines, or an SF5-containing ketimine, with benzyloxyketene in a conrotatory ring closure process. Imine formation and cyclization were possible in spite of the acidification of protons on the carbon bound to SF5. The reactions of the aldimines demonstrated very good 1,2-lk diastereoselectivity, however lack of stereochemical control of the C-N ketimine geometry was reflected in the stereochemistry of the product β-lactam. Cyclization of imines with a stereogenic center bearing SF5 was reflected in the 1,2-lk,lk selectivity of the β-lactam.
authors.affiliation: Department of Chemistry, University at Albany, SUNY, 1400 Washington Ave., Albany, NY 12222, USA.
authors.forename: Alexander
authors.initials: A
authors.lastname: Penger
authors.affiliation: Department of Chemistry, University at Albany, SUNY, 1400 Washington Ave., Albany, NY 12222, USA.
authors.forename: Cortney N
authors.initials: CN
authors.lastname: von Hahmann
authors.affiliation: Department of Chemistry, University at Albany, SUNY, 1400 Washington Ave., Albany, NY 12222, USA.
authors.forename: Alexander S
authors.initials: AS
authors.lastname: Filatov
authors.affiliation: Department of Chemistry, University at Albany, SUNY, 1400 Washington Ave., Albany, NY 12222, USA.
authors.forename: John T
authors.initials: JT
authors.lastname: Welch
keywords: Cornforth transition state; aldimine; diastereoselectivity; organo-fluorine; α-pentafluorosulfanyl aldehyde; β-lactam