Addition of cyclopentadiene and 2-trimethylsilyloxyfuran to quinones bearing a menthyl ester chiral auxiliary

被引:18
作者
Brimble, MA [1 ]
Duncalf, LJ
Reid, DCW
Roberts, TRR
机构
[1] Univ Sydney, Sch Chem, Sydney, NSW 2006, Australia
[2] Univ Auckland, Dept Chem, Auckland, New Zealand
[3] Massey Univ, Dept Chem & Biochem, Palmerston North, New Zealand
关键词
D O I
10.1016/S0040-4020(98)00211-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Addition of cyclopentadiene to 2-carbomethoxy-1,4-benzoquinone 9 afforded Diels-Alder adduct 10 using the Lewis acids ZnCl2 and ZnBr2 whereas the fragmenatation product 11 was the major product when using SnCl4 and TiCl4. 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 ZnCl2 and ZnBr2 as Lewis acids. Use of TiCl4 and SnCl4 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. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5363 / 5374
页数:12
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