107259-69-8Relevant articles and documents
ASYMMETRIC CYCLIZATION OF UNSATURATED ALDEHYDES CATALYZED BY A CHIRAL LEWIS ACID
Sakane, Soichi,Maruoka, Keiji,Yamamoto, Hisashi
, p. 2203 - 2210 (2007/10/02)
A highly enantioselective cyclization of unsaturated aldehydes has been accomplished with the chiral zinc reagent 1 derived from dimethylzinc and (R)-(+)-1,1'-bi-2-naphthol.Thus, the Aldehyde 2 and 10 are treated with the reagent 1 producing the trans alcohol 3 and 11, respectively, with high optical purity (>90percent ee).In sharp contrast, the aldehyde 8 affords the totally racemic alcohol 9.Since the chiral zinc reagent 1 possesses its C2-symmetry, either enantiomer can be prepared from the unsaturated aldehyde by choosing the chiral ligand, (R)-(+)- or (S)-(-)-1,1'-bi-2-naphthol.