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
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Green Chemistry
ISSN: 1463-9262 , E-ISSN: 1463-9270 |
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| Output data | Year: 2014, Volume: 16, Number: 3, Article number : 1521, Pages count : DOI: 10.1039/c3gc41647j | ||||
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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
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 |