475272-56-1Relevant articles and documents
A General C(sp3)-C(sp3) Cross-Coupling of Benzyl Sulfonylhydrazones with Alkyl Boronic Acids
Merchant, Rohan R.,Lopez, Jovan A.
supporting information, p. 2271 - 2275 (2020/03/13)
A general transition-metal-free cross-coupling between benzylic sulfonylhydrazones and 1°, 2°, or 3° alkyl boronic acids is reported. The base-promoted reaction is operationally simple and exhibits a broad substrate scope to forge a variety of alkyl-alkyl bonds, including between sterically encumbered secondary and tertiary sp3-carbons. The ability of this method to simplify retrosynthetic analysis is exemplified by the improved synthesis of multiple medicinally relevant scaffolds.
Improved and scalable synthesis of building blocks for the modular synthesis of teraryl-based alpha-helix mimetics
Trobe, Melanie,Breinbauer, Rolf
, p. 509 - 521 (2016/03/19)
The modular synthesis of teraryl-based alpha-helix mimetics can be accomplished by sequential Suzuki-couplings of arylboronic acid building blocks with 4-iodophenyltriflate core-fragments. We report about new synthetic accesses to core fragments featuring
A modular synthesis of teraryl-based α-helix mimetics, part 1: Synthesis of core fragments with two electronically differentiated leaving groups
Peters, Martin,Trobe, Melanie,Tan, Hao,Kleineweischede, Rolf,Breinbauer, Rolf
, p. 2442 - 2449 (2013/04/24)
Teraryl-based α-helix mimetics have proven to be useful compounds for the inhibition of protein-protein interactions (PPI). We have developed a modular and flexible approach for the synthesis of teraryl-based α-helix mimetics. Central to our strategy is the use of a benzene core unit featuring two leaving groups of differentiated reactivity in the Pd-catalyzed cross-coupling used for terphenyl assembly. With the halogen/diazonium route and the halogen/triflate route, two strategies have successfully been established. The synthesis of core building blocks with aliphatic (Ala, Val, Leu, Ile), aromatic (Phe), polar (Cys, Lys), hydrophilic (Ser, Gln), and acidic (Glu) amino acid side chains are reported. Turn on: Teraryl-based α-helix mimetics can be effectively produced by sequential Suzuki coupling of a central core fragment featuring electronically differentiated leaving groups with aryl boronic pinacol esters (see scheme; dppf=1,1′-bis(diphenylphosphino) ferrocene, DME=dimethoxyethane, Pin=pinacol, Tf=trifluoromethanesulfonyl). With a set of only 2×18 building blocks, all permutations of α-helix mimetics can be produced. Copyright
