By Nicole Jung, Matthias Wiehn, Stefan Bräse (auth.), Stefan Bräse (eds.)
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"This ebook, written through a global crew of popular specialists of their respective box, covers fresh advances in vital subject matters concerning combinatorial chemistry on strong helps. … it is going to be an invaluable addition to the assessment literature and may be of curiosity to an important section of peers operating in SPOC." (Rolando Perez-Pineiro and Hicham Fenniri, JACS, Vol. one hundred thirty (13), 2008)
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Extra info for Combinatorial Chemistry on Solid Supports
Depending on the nature of the resin-bound substrates, cleavage protocols can provide an (additional) alkene functionality 447 or compounds 448 that are substituted by nucleophiles on the sulfone anchoring side. 50 N. Jung et al. Scheme 66 Cleavage possibilities from sulfone linkers It was proven earlier by Janda et al. that resin 394 can be alkylated by various alkylbromines to give either secondary or tertiary carbon centers. These compounds can be cleaved to give alkanes by the use of quite harsh reaction conditions like Raney–Nickel .
Multifunctional Linkers for Combinatorial Solid Phase Synthesis 19 Scheme 18 Multifunctional cleavage of allylic esters type B or non-cyclic substitution products. C-Nucleophiles as well as heteroatomnucleophiles 113 work in this strategy and give product yields of about 80% for ﬁve steps starting from the carboxylic acid resin. The allylic linker core 112 is formed via a two step synthetic route including addition of diethylmalonate to Merriﬁeld resin and decarboxylation. Substrates for allylic substitution can be attached to the carboxylic acid linker via DIC/DMAP mediated coupling reaction.
Jung et al. Scheme 34 Release of amines from resin-bound carbamates azines. These could be released with yields from 82% to quantitative yield in the presence of TFA/CH2 Cl2 (1 : 1). 2 Carbamates Type B In comparison to carbamates type A, carbamates of general structure B are not very often used linkers (Fig. 10, [200, 202]). There are only a few cleavage reactions that are known for producing functional diversity. Fig. 10 Known linker structures of carbamate type B Linker 228 (Fig. 10 and Scheme 35) has been synthesized following a procedure of Wang et al.
Combinatorial Chemistry on Solid Supports by Nicole Jung, Matthias Wiehn, Stefan Bräse (auth.), Stefan Bräse (eds.)