Enantioselective conjugate radical addition reactions mediated by chiral Lewis acid complexes of (R,R)-4,6-dibenzofurandiyl-2,2′-bis(4-phenyloxazoline) (DBFOX/Ph)
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Iserloh, U
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机构:Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Iserloh, U
Curran, DP
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Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USAUniv Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Curran, DP
[1
]
Kanemasa, S
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机构:Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Kanemasa, S
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[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
[2] Kyushu Univ, Inst Adv Mat Study, Kasuga, Fukuoka 8168580, Japan
A high-yielding synthesis (50% overall yield) of tridentate bisoxazoline ligand (R,R)-4,6-dibenzofurandiyl-2,2'-bis(4-phenyloxazoline) (DBFOX/Ph) was developed. DBFOX/Ph was subsequently tested in enantioselective conjugate radical additions onto 3-(3-phenyl-2-propenoyl)-2-oxazolidinone Two dozen Lewis acids were evaluated, and Mg(ClO4)(2) emerged as the best Lewis acid in terms of yield and enantioselectivity (100% yield, 75.4% ee (S)). (C) 1999 Elsevier Science Ltd. All rights reserved.
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页码:2417 / 2428
页数:12
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