Highly enantioselective conjugate additions to alpha,beta-unsaturated ketones catalyzed by a (salen)Al complex.
Chiral (salen)Al complex 1a catalyzes the highly enantioselective conjugate addition of carbon- and nitrogen-based nucleophiles to acyclic alpha,beta-unsaturated ketones. This methodology is tolerant of substantial variation of the ketone structure, providing access to a wide range of useful chiral building blocks in high yield and enantiomeric excess. Synthetic manipulations of the conjugate addition products are demonstrated, including the straightforward preparation of beta-amino ketones and highly enantioenriched carbo- and heterocyclic compounds.
Taylor
Mark S
MS
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Zalatan
David N
DN
Lerchner
Andreas M
AM
Jacobsen
Eric N
EN
D000473:Alkanes / Q000737:chemistry; D000535:Aluminum / Q000737:chemistry*; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D005029:Ethylenediamines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000473:Alkanes; D001386:Azides; D005029:Ethylenediamines; D007659:Ketones; D009570:Nitriles; D009942:Organometallic Compounds; C007972:hydrazoic acid; C011452:disalicylaldehyde ethylenediamine; D000535:Aluminum