ChemInform Abstract: Enantioselective Allylation of Aldehydes Catalyzed by Diastereoisomeric Bis(tetrahydroisoquinoline) N,N′‐Dioxides.

Abstract

Enantioselective Allylation of Aldehydes Catalyzed by Diastereoisomeric Bis(tetrahydroisoquinoline) N,N'-Dioxides. -Asymmetric allylation of aromatic (I) and α,β-unsaturated aldehydes (IV) with allyltrichlorosilane (II) proceeds smoothly in THF in the presence of (Sax)-bis(tetrahydroisoquinoline N-oxide) to give the products (III) and (V) in good yields and moderate to high enantioselectivity. Interestingly, the corresponding (R ax )-ligand does not catalyze this reaction in THF but needs MeCN or CH2Cl2 as solvents to give the products with the same sense of stereoinduction but lower enantioselectivity. -(VLASANA, K.; HRDINA, R.; VALTEROVA, I.; KOTORA*, M.; Eur.