Journal
CHINESE JOURNAL OF ORGANIC CHEMISTRY
Volume 41, Issue 10, Pages 4039-4049Publisher
SCIENCE PRESS
DOI: 10.6023/cjoc202105055
Keywords
asymmetric synthesis; 3,4-dihydrocoumarin; ortho-hydroxyphenyl-substituted para-quinone methide; beta-keto acylpyrazole; organocatalysis
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An organocatalyzed asymmetric formal [4+2] annulation of ortho-hydroxyl functionalized p-quinone methides with beta-keto acylpyrazoles has been developed, providing an efficient approach to access optically active 3,4-dihydrocoumarins. The reactions demonstrate good yields, high levels of diastereo- and enantio-selectivities under mild reaction conditions.
An organocatalyzed asymmetric formal [4+2] annulation of ortho-hydroxyl functionalized p-quinone methides with beta-keto acylpyrazoles has been developed, which provides an efficient approach to access optically active 3,4-dihydrocoumarins. Under the catalysis of a quinine-derived bifunctional squramide, the reactions of a wide range of ortho-hydroxy-phenyl substituted p-quinone methides and beta-keto acylpyrazoles took place smoothly to generate the corresponding polysubstituted 3,4-dihydrocoumarins in good yields with high levels of diastereo- and enantio-selectivities (up to 96% yield, >19/1 dr and 98% ee) under mild reaction conditions.
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