title: Construction of bicyclo[3.2.1]octanes with four stereogenic centers by organocatalytic domino Michael/Aldol reaction.
abstract: An enantio- and diastereoselective organocatalytic domino Michael/Aldol reaction for the direct preparation of synthetically and medicinally relevant bicyclo[3.2.1]octane derivatives with four stereogenic centers, including two quaternary carbons, has been described. The reaction tolerates a large variety of substituents on β,γ-unsaturated 1,2-ketoesters and cyclic 1,3-ketoesters. It allows for the formation of various bicyclo[3.2.1]octanes in good yields (53-98%), diastereoselectivities (1:1 to 5:1 dr), and enantioselectivities (up to 95:5 ee).
authors.affiliation: Department of Organic Chemistry, University of Geneva , quai Ernest Ansermet 30, CH-1211 Geneva 4, Switzerland.
authors.forename: A
authors.initials: A
authors.lastname: Lefranc
authors.forename: L
authors.initials: L
authors.lastname: Gremaud
authors.forename: A
authors.initials: A
authors.lastname: Alexakis