Investigation of Squaramide Catalysts in the Aldol Reaction en Route to Funapide
نویسندگان
چکیده
Funapide is a 3,3’-spirocyclic oxindole with promising analgesic activity. A reported pilot-plant scale synthesis of this chiral compound involves an asymmetric aldol reaction, catalyzed by common bifunctional thiourea structure. In work, we show that the swapping unit catalyst for tailored squaramide group provides equally active, but rewardingly more selective, reaction (from 70.5 to 85 % ee). The was studied first on model compound. Then, set optimal conditions applied target funapide intermediate. applicability these seems limited oxindoles bearing 3-substituent funapide. Exemplifying characteristics target-focused methodological development, study highlights how wide-range screening catalysts and can provide non-negligible improvements in industrially viable transformation.
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ژورنال
عنوان ژورنال: European Journal of Organic Chemistry
سال: 2021
ISSN: ['1434-193X', '1099-0690']
DOI: https://doi.org/10.1002/ejoc.202101254