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Access to Chiral Chromenones through Organocatalyzed Mannich/Annulation Sequence.

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Herein we report an efficient and practical method to access chiral chromenones bearing one α-amino stereogenic center in the β position of the carbonyl group. The quinine-derived squaramide could efficiently… Click to show full abstract

Herein we report an efficient and practical method to access chiral chromenones bearing one α-amino stereogenic center in the β position of the carbonyl group. The quinine-derived squaramide could efficiently promote Mannich/cycloketalization/dehydration tandem reactions between 1-(2-hydroxyaryl)-1,3-diketones and functionalized imines generated in situ, providing a wide range of chiral chromenones with propargylamine or α-amino ester moieties with good results (54 examples, up to 98% ee).

Keywords: organocatalyzed mannich; mannich annulation; access chiral; chromenones organocatalyzed; chiral chromenones

Journal Title: Organic letters
Year Published: 2021

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