Chiral NHC-catalyzed oxodiene Diels-Alder reactions with alpha-chloroaldehyde bisulfite salts.
Alpha-chloroaldehyde bisulfite adducts were successfully employed in chiral NHC-catalyzed hetero-Diels-Alder reactions with various oxodienes under biphasic reaction conditions with high levels of enantioselectivity. This new protocol makes possible enantioselective additions from commercially available chloroacetaldehyde sodium bisulfite and demonstrates that this unique class of catalysts readily tolerates aqueous conditions.
He
Ming
M
Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106-9510, USA.
Beahm
Brendan J
BJ
Bode
Jeffrey W
JW
D000447:Aldehydes / Q000737:chemistry*; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism; D013447:Sulfites / Q000737:chemistry
D000447:Aldehydes; D006571:Heterocyclic Compounds; D006843:Hydrocarbons, Chlorinated; D007783:Lactones; D013447:Sulfites; C030011:carbene; C042345:hydrogen sulfite; D008697:Methane