Abstract: Simple enantiomerically pure C2-symmetric quinoline (isoquinoline)-derived 1,2-diamines were synthesized from the corresponding aldehydes via stereospecific diaza-Cope rearrangement with 2,2′-(1,2-diaminoethane-1,2-diyl)diphenol (HPEN). Efficient green synthesis of both enantiomers of the anticoagulant Warfarin and rodenticide Coumachlor was achieved in an aqueous medium via the asymmetric iminium-type Michael reaction in the presence of the catalysts 8e and (ent)-8e in combination with (R)- or (S)-mandelic acid, respectively. This procedure provides high enantioselectivity (up to 91% ee), which has never been attained for these bioactive compounds with the known catalysts under aqueous conditions. Nearly optically pure Warfarin (∼99% ee) was prepared via a green isolation procedure, which included acidic precipitation of the crude product from a basic aqueous solution followed by single recrystallization. Furthermore, unlike the known primary amine-derived organocatalysts, the developed aqueous catalytic system does not produce parasitic byproducts and can be recovered and reused in the asymmetric reaction.

Cite: Kucherenko A. , Kostenko A. , Zhdankina G.M. , Kuznetsova O.Y. , Zlotin S.G.
Green asymmetric synthesis of Warfarin and Coumachlor in pure water catalyzed by quinoline-derived 1,2-diamines
Green Chemistry. 2018. V.20. N3. P.754-759. DOI: 10.1039/c7gc03626d WOS Scopus OpenAlex

Identifiers:

Web of science:	WOS:000424276300024
Scopus:	2-s2.0-85041392061
OpenAlex:	W2781984535

Citing:

DB	Citing
OpenAlex	28
Scopus	28
Web of science	26

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