Abstract

Addition of cyclopentadiene to 2-carbomethoxy-1,4-benzoquinone 9 afforded Diels-Alder adduct 10 using the Lewis acids ZnCl 2 and ZnBr 2 whereas the fragmenatation product 11 was the major product when using SnCl 4 and TiCl 4. Addition of cyclopentadiene to 1,4-benzoquinone 8 bearing a menthyl ester at C-2 afforded Diels-alder adduct 12 in moderate diastereomeric excess using ZnCl 2 and ZnBr 2 as Lewis acids. Use of TiCl 4 and SnCl 4 afforded the fragmentation product 13 also in moderate diastereomeric excess. Addition of 2-trimethylsilyloxyfuran to chiral naphthoquinone 4 and benzoquinone 8 afforded furofuran adducts 14 and 15 respectively as a 1:1 mixture of diastereomers.

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