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

Iserloh, U and Curran, DP and Kanemasa, S (1999) Enantioselective conjugate radical addition reactions mediated by chiral Lewis acid complexes of (R,R)-4,6-dibenzofurandiyl-2,2'-bis(4- phenyloxazoline) (DBFOX/Ph). Tetrahedron Asymmetry, 10 (12). 2417 - 2428. ISSN 0957-4166

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Abstract

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(ClO 4 ) 2 emerged as the best Lewis acid in terms of yield and enantioselectivity (100% yield, 75.4% ee (S)).


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Iserloh, U
Curran, DPcurran@pitt.eduCURRAN
Kanemasa, S
Date: 18 June 1999
Date Type: Publication
Journal or Publication Title: Tetrahedron Asymmetry
Volume: 10
Number: 12
Page Range: 2417 - 2428
DOI or Unique Handle: 10.1016/s0957-4166(99)00238-4
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0957-4166
Date Deposited: 18 Jul 2014 21:00
Last Modified: 27 Apr 2019 14:55
URI: http://d-scholarship.pitt.edu/id/eprint/22287

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