Synthesis of 2,3,4-Trisubstituted Thiochromanes using an Organocatalytic Enantioselective Tandem Michael-Henry Reaction

Synthesis of 2,3,4-Trisubstituted Thiochromanes using an Organocatalytic Enantioselective Tandem Michael-Henry Reaction

Enantioenriched 2,3,4‐trisubstituted thiochromanes have been synthesized by using a cupreine‐catalyzed tandem Michael addition–Henry reaction between 2‐mercaptobenzaldehydes and β‐nitrostyrenes. Good diastereoselectivities and enantioselectivities were obtained for the title compounds, which may be...

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Veröffentlicht in:Advanced synthesis & catalysis 2008-03, Vol.350 (4), p.537-541
Hauptverfasser: Dodda, Rajasekhar, Goldman, Joshua J., Mandal, Tanmay, Zhao, Cong-Gui, Broker, Grant A., Tiekink, Edward R. T.
Format: Artikel
Sprache:eng
Schlagworte:
2-mercaptobenzaldehyde
Henry reaction
Michael addition
organocatalysis
tandem reaction
β-nitrostyrene
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Zusammenfassung:Enantioenriched 2,3,4‐trisubstituted thiochromanes have been synthesized by using a cupreine‐catalyzed tandem Michael addition–Henry reaction between 2‐mercaptobenzaldehydes and β‐nitrostyrenes. Good diastereoselectivities and enantioselectivities were obtained for the title compounds, which may be further improved through a single recrystallization (up to 98% de and>99% ee).
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200700331