Towards Sustainable Amino Acid Derived Organocatalysts for Asymmetric syn‐Aldol Reactions

Towards Sustainable Amino Acid Derived Organocatalysts for Asymmetric syn‐Aldol Reactions Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2017, Volume: 2017, Number: 17, Pages: 2540-2544 Pages count : 5 DOI: 10.1002/ejoc.201700166

Authors

Gerasimchuk Vasiliy V. ¹ , Kucherenko Alexandr S. ¹ , Fakhrutdinov Artem N. ¹ , Medvedev Michael G. ² , Nelyubina Yulia V. ² , Zlotin Sergei G. ¹

Affiliations

1	Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russia
2	Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str., 28, 119991 Moscow, Russia

The undesirable side-processes responsible for the fast deactivation of primary amino acid derived organocatalysts in asymmetric aldol reactions are identified. A new ionic-liquid-supported (S)-valine-/(S)-α,α-diphenylserinol-derived catalyst (9) is designed on the basis of these results and exhibits much better recyclability in asymmetric syn-aldol reactions between hydroxyacetone and aldehydes. Furthermore, this catalyst appeared to be useful for the stereoselective synthesis of the naturally occurring 1(3H)-isobenzofuran-1-one scaffold through an asymmetric syn-aldol/lactonization cascade reaction.

Gerasimchuk V.V. , Kucherenko A.S. , Fakhrutdinov A.N. , Medvedev M.G. , Nelyubina Y.V. , Zlotin S.G.
Towards Sustainable Amino Acid Derived Organocatalysts for Asymmetric syn‐Aldol Reactions
European Journal of Organic Chemistry. 2017. V.2017. N17. P.2540-2544. DOI: 10.1002/ejoc.201700166 WOS Scopus OpenAlex

Web of science:	WOS:000400993800018
Scopus:	2-s2.0-85019039251
OpenAlex:	W2593041555

DB	Citing
OpenAlex	13
Scopus	15
Web of science	12