Chiral Bis(8-Quinolyl)Ethane-Derived Diimine: Structure Elucidation and Catalytic Performance in Asymmetric Synthesis of (S)-Warfarin

Chiral Bis(8-Quinolyl)Ethane-Derived Diimine: Structure Elucidation and Catalytic Performance in Asymmetric Synthesis of (S)-Warfarin Научная публикация

Журнал

Catalysts
ISSN: 2073-4344

Вых. Данные

Год: 2023, Том: 13, Номер: 1, Номер статьи : 136, Страниц : DOI: 10.3390/catal13010136

Авторы

Nikitin Ilya D. ^1,2 , Kovalevsky Ruslan A. ^3,1 , Kucherenko Alexander S. ¹ , Kuznetsova Olga Y. ¹ , Zlotin Sergei G. ¹

Организации

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, 119991 Moscow, Russia
2	Nelubin Institute of Pharmacy, Sechenov First Moscow State Medical University, Trubetskaya Str. 8/2, 119991 Moscow, Russia
3	Department of Chemistry, Moscow State University, Leninskie Gory 1-3, 119234 Moscow, Russia

C2-symmetric diimine generated in situ from (R,R)-HPEN and 8-formylquinoline was readily transformed to novel chiral diimine pre-III bearing 1(S),2(S)-bis(quinolin-8-yl) ethane and salicylic aldehyde fragments via stereoselective diaza-Cope rearrangement. The structure and absolute configuration of the product was established by the X-ray diffraction study of the corresponding Rh(III) complex. In the presence of pre-III, practically important enantioselective reactions of 4-hydroxycoumarin with α,β-enones afforded anticoagulant (S)-warfarin and its derivatives in aqueous THF in high yield (88–92%) with enantioselectivity 85–93% ee.

Nikitin I.D. , Kovalevsky R.A. , Kucherenko A.S. , Kuznetsova O.Y. , Zlotin S.G.
Chiral Bis(8-Quinolyl)Ethane-Derived Diimine: Structure Elucidation and Catalytic Performance in Asymmetric Synthesis of (S)-Warfarin
Catalysts. 2023. V.13. N1. 136 . DOI: 10.3390/catal13010136 WOS Scopus OpenAlex

Web of science:	WOS:000914719400001
Scopus:	2-s2.0-85146674328
OpenAlex:	W4313890927

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OpenAlex	1
Scopus	1
Web of science	1