65926-39-8Relevant articles and documents
Alkyl Carbagermatranes Enable Practical Palladium-Catalyzed sp2-sp3 Cross-Coupling
Xu, Meng-Yu,Jiang, Wei-Tao,Li, Ying,Xu, Qing-Hao,Zhou, Qiao-Lan,Yang, Shuo,Xiao, Bin
supporting information, p. 7582 - 7588 (2019/05/16)
Pd-catalyzed cross-coupling reactions have achieved tremendous accomplishments in the past decades. However, C(sp3)-hybridized nucleophiles generally remain as challenging coupling partners due to their sluggish transmetalation compared to the C(sp2)-hybridized counterparts. While a single-electron-transfer-based strategy using C(sp3)-hybridized nucleophiles had made significant progress recently, fewer breakthroughs have been made concerning the traditional two-electron mechanism involving C(sp3)-hybridized nucleophiles. In this report, we present a series of unique alkyl carbagermatranes that were proven to be highly reactive in cross-coupling reactions with our newly developed electron-deficient phosphine ligands. Generally, secondary alkyl carbagermatranes show slightly lower, yet comparable activity to its Sn analogue. Meanwhile, primary alkyl carbagermatranes exhibit high activity, and they were also proved stable enough to be compatible with various reactions. Chiral secondary benzyl carbagermatrane gave the coupling product under base/additive-free conditions with its configuration fully inversed, suggesting that transmetalation was carried out in an "SE2(open) Inv" pathway, which is consistent with Hiyama's previous observation. Notably, the cross-coupling of primary alkyl carbagermatranes could be performed under base/additive-free conditions with excellent functional group tolerance and therefore may have potentially important applications such as stapled peptide synthesis.
Structure-based design and synthesis of phosphinate isosteres of phosphotyrosine for incorporation in Grb2-SH2 domain inhibitors. Part 2
Walker, Clive V.,Caravatti, Giorgio,Denholm, Alastair A.,Egerton, John,Faessler, Alex,Furet, Pascal,Garcia-Echeverria, Carlos,Gay, Brigitte,Irving, Ed,Jones, Ken,Lambert, Amanda,Press, Neil J.,Woods, John
, p. 2343 - 2346 (2007/10/03)
A series of novel phosphinates, derived from 4-phosphonomethylphenylalanine, are described as isosteres of phosphotyrosine. Benzyl (or alkyl) phosphinomethylphenylalanine derivatives were prepared by alkylation of an amino acid P-H phosphinate. (C) 2000 Elsevier Science Ltd.
Applications of Radical Addition Reactions to the Synthesis of a C-Glucoside and a Functionalised Amino-acid
Adlington, Robert M.,Baldwin, Jack E.,Basak, Amit,Kozyrod, Robert P.
, p. 944 - 945 (2007/10/02)
Addition of carbon radicals derived from tetra-acetylglucosyl and β-alanyl derivatives to acrylic acid or esters provides a short route to a C-glucoside and a functionalised α-amino-acid, respectively.
