24464-69-5Relevant academic research and scientific papers
Structurally Diverse Acyl Bicyclobutanes: Valuable Strained Electrophiles
Attard, Riley H.,Gardiner, Michael G.,Malins, Lara R.,Schwartz, Brett D.,Zhang, Meng Yao
, p. 2808 - 2812 (2020)
Bicyclo[1.1.0]butanes (BCBs) are highly strained carbocycles that have emerged as versatile synthetic tools, particularly for the construction of functionalized small molecules. This work reports two efficient pathways for the rapid preparation of over 20 structurally diverse BCB ketones, encompassing simple alkyl and aryl derivatives, as well as unprecedented amino acid, dipeptide, bioisostere, and bifunctional linchpin reagents currently inaccessible using literature methods. Analogues are readily forged in two steps and in high yields from simple carboxylic acids or through unsymmetrical ketone synthesis beginning with a convenient carbonyl dication equivalent. The utility of this novel toolbox of strained electrophiles for the selective modification of proteinogenic nucleophiles is highlighted.
Strain-Release [2π+ 2σ] Cycloadditions for the Synthesis of Bicyclo[2.1.1]hexanes Initiated by Energy Transfer
Braley, Sarah E.,Brown, M. Kevin,Chang, Yu-Che,Fessard, Thomas C.,Guo, Renyu,Herter, Loic,Salome, Christophe
, (2022/05/11)
Saturated bicycles are becoming ever more important in the design and development of new pharmaceuticals. Here a new strategy for the synthesis of bicyclo[2.1.1]hexanes is described. These bicycles are significant because they have defined exit vectors, yet many substitution patterns are underexplored as building blocks. The process involves sensitization of a bicyclo[1.1.0]butane followed by cycloaddition with an alkene. The scope and mechanistic details of the method are discussed.
Investigating Bicyclobutane-Triazolinedione Cycloadditions as a Tool for Peptide Modification
Schwartz, Brett D.,Smyth, Aidan P.,Nashar, Philippe E.,Gardiner, Michael G.,Malins, Lara R.
, p. 1268 - 1273 (2022/02/07)
Acyl bicyclobutanes are shown to engage in strain-promoted cycloaddition reactions with a diverse array of triazolinedione reagents. The synthesis of an orthogonally protected urazole building block enabled the facile preparation of amino acid- and peptid
