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(ClO4)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:	Creators Email Pitt Username ORCID Iserloh, U Curran, DP curran@pitt.edu CURRAN 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:	12 Jun 2021 23:55
URI:	http://d-scholarship-dev.library.pitt.edu/id/eprint/22287

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