2-Nitroallyl carbonate-based green bifunctional reagents for catalytic asymmetric annulation reactions

2-Nitroallyl carbonate-based green bifunctional reagents for catalytic asymmetric annulation reactions Full article

Journal

Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Output data

Year: 2021, Volume: 19, Number: 8, Pages: 1780-1786 Pages count : 7 DOI: 10.1039/d0ob02283g

Authors

Kostenko Alexey A. ¹ , Bykova Kseniya A. ¹ , Kucherenko Alexander S. ¹ , Komogortsev Andrey N. ¹ , Lichitsky Boris V. ¹ , Zlotin Sergei G. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, Moscow, Russian Federation

2-Nitroallylic carbonates, a new class of “green” 1,3-bielectrophilic reagents for organic synthesis and catalysis, have been prepared. The bifunctional tertiary amine-catalyzed asymmetric [3 + 3] annulations of cyclic enols with these reagents occur much faster than corresponding reactions with 2-nitroallylic esters and produce no acidic by-products poisoning the catalyst. Furthermore, 2-nitroallylic carbonates enable highly enantioselective one-pot synthesis of a variety of fused dihydropyrane derivatives from available precursors bearing pharmacophoric fragments.

Kostenko A.A. , Bykova K.A. , Kucherenko A.S. , Komogortsev A.N. , Lichitsky B.V. , Zlotin S.G.
2-Nitroallyl carbonate-based green bifunctional reagents for catalytic asymmetric annulation reactions
Organic & Biomolecular Chemistry. 2021. V.19. N8. P.1780-1786. DOI: 10.1039/d0ob02283g WOS Scopus OpenAlex

Web of science:	WOS:000625235100013
Scopus:	2-s2.0-85102058440
OpenAlex:	W3128110662

DB	Citing
OpenAlex	16
Scopus	16
Web of science	15