title: B-Alkylcatecholborane-mediated tandem radical conjugated addition-aldol cyclization.
abstract: A one-pot procedure involving radical conjugate addition of B-alkylcatecholboranes to enones followed by intramolecular aldol reaction is reported. Application to the stereoselective synthesis of monocyclic and bicyclic products with up to four contiguous stereogenic centers is presented.
authors.affiliation: Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland.
authors.forename: Alice
authors.initials: A
authors.lastname: Beauseigneur
authors.forename: Cecilia
authors.initials: C
authors.lastname: Ericsson
authors.forename: Philippe
authors.initials: P
authors.lastname: Renaud
authors.forename: Kurt
authors.initials: K
authors.lastname: Schenk
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001880:Boranes; D007659:Ketones; C116609:3-hydroxybutanal