Cr(Salen)-catalyzed addition of 1,3-dichloropropene to aromatic aldehydes. A simple access to optically active vinyl epoxides.
[reaction: see text]. Chiral Cr(Salen) complex (1) prepared in situ from CrCl3 promotes the enantioselective addition of 1,3-dichloropropene to aromatic aldehydes in the presence of Mn as the stoichiometric reductant and Me3SiCl as a scavenger. The resulting 1,2-chlorohydrins obtained in good enantiomeric and diastereoisomeric excesses can be easily transformed into the corresponding chiral vinyl epoxides.
Bandini
M
M
Dipartimento di Chimica G. Ciamician, via Selmi 2, 40126, Bologna, Italy.
Cozzi
P G
PG
Melchiorre
P
P
Morganti
S
S
Umani-Ronchi
A
A
D000447:Aldehydes / Q000737:chemistry*; D000498:Allyl Compounds / Q000737:chemistry*; D002712:Chlorides / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D017608:Chromium Compounds / Q000737:chemistry*; D005029:Ethylenediamines / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated; D008345:Manganese / Q000737:chemistry; D008956:Models, Chemical
D000447:Aldehydes; D000498:Allyl Compounds; D002712:Chlorides; D017608:Chromium Compounds; D005029:Ethylenediamines; D006843:Hydrocarbons, Chlorinated; D008345:Manganese; C011452:disalicylaldehyde ethylenediamine; C023891:1,3-dichloro-1-propene; C017133:chromous chloride