Combinatorial Chemistry for Ligand Development in Catalysis:  Synthesis and Catalysis Screening of Peptidosulfonamide Tweezers on the Solid Phase

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 diethylzi...

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Bibliographic Details
Published in:Journal of organic chemistry 2000-03, Vol.65 (6), p.1750-1757
Main Authors: Brouwer, Arwin J, van der Linden, Heiko J, Liskamp, Rob M. J
Format: Article
Language:English
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Summary: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%).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo991628z