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A New Chiral Organosulfur Catalyst for Highly Stereoselective Synthesis of Epoxides
Author(s) -
Gui Yuan,
Li Jian,
Guo ChangShan,
Li XinLiang,
Lu ZhiFeng,
Huang ZhiZhen
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800453
Subject(s) - chemistry , organosulfur compounds , stereoselectivity , catalysis , bromide , organic chemistry , epoxide , enantioselective synthesis , combinatorial chemistry , sulfur
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 ).