Combinatorial chemistry for ligand development in catalysis: synthesis and catalysis screening of peptidosulfonamide tweezers on the solid phase

Brouwer, A.J., van der Linden, H.J. and Liskamp, R.M.J. (2000) Combinatorial chemistry for ligand development in catalysis: synthesis and catalysis screening of peptidosulfonamide tweezers on the solid phase. Journal of Organic Chemistry, 65(6), pp. 1750-1757. (doi:10.1021/jo991628z)

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Abstract

On the basis of a pyrrolidine tweezer 1, a library of peptidosulfonamide tweezers (15a−e, 16a−e) was synthesized on the solid phase. This library was screened in a simultaneous substrate screening procedure for the ability to enantioselectively catalyze the Ti(O-i-Pr)4-mediated addition of diethylzinc to aldehydes. One of the best solid-phase tweezer catalyst (i.e., 16d, giving an ee of 32% in solid-phase catalysis) was resynthesized in solution (compounds 20 and 21). The now homogeneous solution-phase catalysis showed even better enantioselectivity (i.e., up to 66%).

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Liskamp, Professor Robert
Authors: Brouwer, A.J., van der Linden, H.J., and Liskamp, R.M.J.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Organic Chemistry
Publisher:American Chemical Society
ISSN:0022-3263
ISSN (Online):1520-6904

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