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Stereodivergent Michael addition of diphenylphosphite to α-nitroalkenes in the presence of squaramide-derived tertiary amines: an enantioselective organocatalytic reaction in supercritical carbon dioxide Full article

Journal Green Chemistry
ISSN: 1463-9262 , E-ISSN: 1463-9270
Output data Year: 2014, Volume: 16, Number: 3, Article number : 1521, Pages count : DOI: 10.1039/c3gc41647j
Authors Kuchurov Ilya V. 1 , Nigmatov Albert G. 1 , Kryuchkova Evgeniya V. 1 , Kostenko Alexey A. 2 , Kucherenko Alexandr S. 1 , Zlotin Sergei G. 1
Affiliations
1 N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., Moscow 119991, Russia
2 D.I. Mendeleyev University of Chemical Technology of Russia, Miusskaya Campus, 9 Miusskaya square, Moscow 125047, Russia

Abstract: The first “green” asymmetric organocatalytic reaction in a supercritical carbon dioxide medium was elaborated. Under the proposed conditions (100 bar, 35 °C), α-nitroalkenes enantioselectively accept diphenylphosphite in the presence of bifunctional organocatalysts bearing the tertiary amino group and the squaramide fragment to afford corresponding β-nitrophosphonates in high yields and with enantioselectivities of up to 94% ee. By varying the catalyst structure it is possible to synthesize both β-nitrophosphonate enantiomers under these conditions. A significant potential of the supercritical extraction for product isolation and catalyst recovery was demonstrated.
Cite: Kuchurov I.V. , Nigmatov A.G. , Kryuchkova E.V. , Kostenko A.A. , Kucherenko A.S. , Zlotin S.G.
Stereodivergent Michael addition of diphenylphosphite to α-nitroalkenes in the presence of squaramide-derived tertiary amines: an enantioselective organocatalytic reaction in supercritical carbon dioxide
Green Chemistry. 2014. V.16. N3. 1521 . DOI: 10.1039/c3gc41647j WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:000332039200063
Scopus: 2-s2.0-84894620205
OpenAlex: W2105440278
Citing:
DB Citing
OpenAlex 31
Scopus 30
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