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Highly functionalized aldol-type products bearing a beta-quaternary center and a stereoselectively controlled gamma-hydroxy function are readily prepared by the diastereoselective addition of an allylic zinc reagent embedded in an isoxazole ring to various aromatic and heteroaromatic aldehydes, in the presence of Lewis acids, such as MgCl2 or LaCl32 LiCl. After reductive cleavage of the N=O bond by using Fe, NH4Cl, aldol-type products bearing a stereocontrolled beta-quaternary center and a gamma-hydroxy group were observed. The benzylic reactivity of the isoxazolylmethylzinc reagent towards other electrophiles, such as acid chlorides, aryl and allylic halides, as well as aldehydes in the presence of BF3OEt2 are also described. Highly functionalized aldol-type products bearing a beta-quaternary center and a stereoselectively controlled gamma-hydroxy function are readily prepared by the diastereoselective addition of an allylic zinc reagent to various aromatic and heteroaromatic aldehydes in the presence of Lewis acids MgCl2 or LaCl32 LiCl (see scheme).
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Reference：
Benzofuran – Wikipedia,
Benzofuran | C8H885O – PubChem