A New Chiral Organosulfur Catalyst for Highly Stereoselective Synthesis of Epoxides

A New Chiral Organosulfur Catalyst for Highly Stereoselective Synthesis of Epoxides

A new chrial organosulfide was synthesized through an unexpected Wagner–Meerwein rearrangement. This organosulfide could catalyze the epoxidation reaction of various aromatic aldehydes smoothly with benzyl bromide to give trans‐diaryl epoxides in satisfactory yields (60–84%) with excellent diastereo...

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Veröffentlicht in:Advanced synthesis & catalysis 2008-11, Vol.350 (16), p.2483-2487
Hauptverfasser: Gui, Yuan, Li, Jian, Guo, Chang‐Shan, Li, Xin‐Liang, Lu, Zhi‐Feng, Huang, Zhi‐Zhen
Format: Artikel
Sprache:eng
Schlagworte:
chiral organosulfides
diastereoselectivity
enantioselectivity
epoxidation
organocatalysis
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Zusammenfassung:A new chrial organosulfide was synthesized through an unexpected Wagner–Meerwein rearrangement. This organosulfide could catalyze the epoxidation reaction of various aromatic aldehydes smoothly with benzyl bromide to give trans‐diaryl epoxides in satisfactory yields (60–84%) with excellent diastereoselectivities (trans:cis=95:5–100:0) and good to excellent enantioselectivities (86–96% ee).
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200800453