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Abstract
Treatment of anthracenebisresorcinol (1·4H) with La(OiPr)3 and binaphthol (BN·2H) as a chiral ligand affords an amorphous and insoluble 1:2:2 adduct (chiral La host) formulated as (1·2H)2-·2(LaBN)+. This formulation suggests that chiral La3+-binaphthoxide moieties are attached to the half-deprotonated hydrogen-bonded network of the host. The chiral La host catalyzes the Michael reaction of dimethyl malonate with cyclohexenone with ee ≡ 70%. The analogous chiral Al host (1·2H)2-·2(AlBN)+ obtained from Al(CH3)3 catalyzes the Diels-Alder reaction between N-crotonoyl-1,3-oxazolidin-2-one and cyclopentadiene with an ee of ∼75% for the minor exo product.