Highly diastereoselective tandem photoenolization-hetero-diels-alder cycloaddition reactions of o-tolualdehydes in the solid state

…, P Mal, N Singhal, P Venkatakrishnan…

文献索引：Moorthy, Jarugu Narasimha; Mal, Prasenjit; Singhal, Nidhi; Venkatakrishnan, Parthasarathi; Malik, Ravish; Venugopalan, Paloth Journal of Organic Chemistry, 2004 , vol. 69, # 24 p. 8459 - 8466

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被引用次数: 16

摘要

The (E)-photoenols generated in situ by photolysis of o-tolualdehydes 1-5 in the solid state react with the precursor aldehydes as dienophiles in a hetero-Diels-Alder cycloaddition fashion to afford trans-3-arylisochromanols in excellent yields and in a high diastereoselectivity. An examination of the reactivity of three different classes of rationally designed aldehydes shows that the tandem enolization-Diels-Alder cycloaddition occurs ...