(1,2-Diaminoethane-1,2-diyl)bis(N-methylpyridinium) Salts as a Prospective Platform for Designing Recyclable Prolinamide-Based Organocatalysts

(1,2-Diaminoethane-1,2-diyl)bis(N-methylpyridinium) Salts as a Prospective Platform for Designing Recyclable Prolinamide-Based Organocatalysts Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2015, Volume: 80, Number: 19, Pages: 9570-9577 Pages count : 8 DOI: 10.1021/acs.joc.5b01555

Authors

Lisnyak Vladislav G. ^1,2 , Kucherenko Alexander S. ¹ , Valeev Edward F. ³ , Zlotin Sergei G. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, 119991 Moscow, Russia
2	Higher Chemical College of the Russian Academy of Sciences, D. I. Mendeleev University of Chemical Technology, 9 Miusskaya Square, 125047 Moscow, Russia
3	Department of Chemistry, Virginia Tech, Blacksburg, Virginia 24061, United States

A new efficient and highly recyclable organocatalyst has been developed for asymmetric cross-aldol reactions under neat conditions in ketone–ketone, ketone–aldehyde, and aldehyde–aldehyde systems. The catalyst features two prolinamide fragments and a C2-symmetrical (1,2-diaminoethane-1,2-diyl)bis(N-methylpyridinium) group. The catalyst retained high activity and excellent stereoselection over the operating period of more than 830 h (25 cycles). An ab initio theoretical investigation explained the absolute configuration of the products and different stereoinduction levels for designed diastereomeric organocatalysts.

Lisnyak V.G. , Kucherenko A.S. , Valeev E.F. , Zlotin S.G.
(1,2-Diaminoethane-1,2-diyl)bis(N-methylpyridinium) Salts as a Prospective Platform for Designing Recyclable Prolinamide-Based Organocatalysts
Journal of Organic Chemistry. 2015. V.80. N19. P.9570-9577. DOI: 10.1021/acs.joc.5b01555 WOS Scopus OpenAlex

Web of science:	WOS:000362386400019
Scopus:	2-s2.0-84942924484
OpenAlex:	W2395885076

DB	Citing
OpenAlex	27
Scopus	33
Web of science	31