Mechanistic investigations in diastereoselective Diels–Alder additions of chiral 9-anthrylethanol derivatives

JCC Atherton, S Jones

文献索引：Atherton, J. C. Christian; Jones, Simon Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 19 p. 2166 - 2173

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被引用次数: 27

摘要

The preparation and subsequent Diels–Alder addition reactions of chiral 9-functionalised anthracene derivatives have been investigated. 9-(1-Methoxyethyl) anthracene undergoes highly diastereoselective (> 95∶ 5) thermal and photoinduced Diels–Alder additions with maleic anhydride and N-methylmaleimide. The corresponding reactions of 1-anthracen-9- ylethanol occur with the reverse sense of selectivity for additions with maleic anhydride ...