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Asymmetric Sulfoxidation of Thioethers with Hydrogen Peroxide in Water Mediated by Platinum Chiral Catalyst
Author(s) -
Scarso Alessandro,
Strukul Giorgio
Publication year - 2005
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.200505030
Subject(s) - chemistry , catalysis , hydrogen peroxide , platinum , sulfoxide , sulfone , stereoselectivity , aryl , organic chemistry , diethyl ether , ether , alkyl , pulmonary surfactant , medicinal chemistry , biochemistry
Easy stereoselective oxidation of prochiral aryl alkyl sulfides 2 to the corresponding sulfoxides can be achieved in water‐surfactant medium with inexpensive hydrogen peroxide mediated by the chiral platinum diphosphine complex {[( R )‐BINAP]Pt(μ ‐ OH)} 2 (BF 4 ) 2 ( 1 ). Remarkable key features of general interest are (i) easy isolation of the products from catalyst by simple diethyl ether/water‐surfactant two phase separation, (ii) catalyst loading as low as 1% mol, (iii) good yields, sulfoxide 3 to sulfone 4 ratio up to 200 : 1 and enantioselectivities up to 88%, (iv) mild experimental conditions.
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