B-Alkylcatecholborane-mediated tandem radical conjugated addition-aldol cyclization.
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.
Beauseigneur
Alice
A
Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland.
Ericsson
Cecilia
C
Renaud
Philippe
P
Schenk
Kurt
K
D000447:Aldehydes / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D001880:Boranes; D007659:Ketones; C116609:3-hydroxybutanal