Enantioselective conjugate radical addition reactions mediated by chiral Lewis acid complexes of (R,R)-4,6-dibenzofurandiyl-2,2 '-bis(4-phenyloxazoline) (DBFOX/Ph)

Authors
Iserloh, U Curran, DP Kanemasa, S
Citation
U. Iserloh et al., Enantioselective conjugate radical addition reactions mediated by chiral Lewis acid complexes of (R,R)-4,6-dibenzofurandiyl-2,2 '-bis(4-phenyloxazoline) (DBFOX/Ph), TETRAHEDR-A, 10(12), 1999, pp. 2417-2428
Citations number
28
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
12
Year of publication
1999
Pages
2417 - 2428
Database
ISI
SICI code
0957-4166(19990618)10:12<2417:ECRARM>2.0.ZU;2-6
Abstract
A high-yielding synthesis (50% overall yield) of tridentate bisoxazoline li gand (R,R)-4,6-dibenzofurandiyl-2,2'-bis(4-phenyloxazoline) (DBFOX/Ph) was developed. DBFOX/Ph was subsequently tested in enantioselective conjugate r adical additions onto 3-(3-phenyl-2-propenoyl)-2-oxazolidinone Two dozen Le wis 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.