title: Highly diastereo- and enantioselective organocatalytic domino Michael/aldol reaction of acyclic 3-halogeno-1,2-diones to α,β-unsaturated aldehydes.
abstract: The first organocatalytic diastereo- and enantioselective domino Michael/aldol reaction of 3-halogeno-1,2-diones to α,β-unsaturated aldehydes has been achieved. This transformation tolerates a large variety of electronically different substituents on both reactive partners and allows the synthesis of challenging cyclopentanone derivatives with four contiguous stereogenic centers in excellent diastereoselectivities (>20:1 dr) as well as good yields (69-97%), and enantioselectivities (up to 94% ee).
authors.affiliation: Department of Organic Chemistry, University of Geneva, quai Ernest Ansermet 30, CH-1211 Geneva 4, Switzerland.
authors.forename: Alice
authors.initials: A
authors.lastname: Lefranc
authors.forename: Laure
authors.initials: L
authors.lastname: Guénée
authors.forename: Alexandre
authors.initials: A
authors.lastname: Alexakis