Highly enantioselective Michael addition of cyclohexanone to nitroolefins catalyzed by pyrrolidine-based bifunctional benzoylthiourea in water

Autor:	Qing-Shan Li, Mengchen Yang, Shu-Rong Ban, Zhenyu Wang
Rok vydání:	2016
Předmět:	Pharmacology 010405 organic chemistry Organic Chemistry Enantioselective synthesis Cyclohexanone 010402 general chemistry 01 natural sciences Catalysis Pyrrolidine 0104 chemical sciences Analytical Chemistry chemistry.chemical_compound chemistry Organocatalysis Drug Discovery Michael reaction Organic chemistry Organic synthesis Bifunctional Spectroscopy
Zdroj:	Chirality. 28:721-727
ISSN:	0899-0042
DOI:	10.1002/chir.22648
Popis:	Organocatalysis and aqueous reactions are identified as the focus of the greening of chemistry. Combining these two strategies effectively remains an interesting challenge in organic synthesis. Herein, we used pyrrolidine-based benzoylthiourea 1c to catalyze the asymmetric Michael addition of cyclohexanone to various nitroolefins in water to afford the corresponding compounds in moderate to good yields, and with excellent diastereoselectivities (up to >99:1 dr) and enantioselectivities (up to 99% ee).
Databáze:	OpenAIRE
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