114701-81-4Relevant articles and documents
Vinylidene Homologation of Boronic Esters and its Application to the Synthesis of the Proposed Structure of Machillene
Fordham, James M.,Grayson, Matthew N.,Aggarwal, Varinder K.
, p. 15268 - 15272 (2019)
Alkenyl boronic esters are important reagents in organic synthesis. Herein, we report that these valuable products can be accessed by the homologation of boronic esters with lithiated epoxysilanes. Aliphatic and electron-rich aromatic boronic esters provided vinylidene boronic esters in moderate to high yields, while electron-deficient aromatic and vinyl boronic esters were found to give the corresponding vinyl silane products. Through DFT calculations, this divergence in mechanistic pathway has been rationalized by considering the stabilization of negative charge in the C?Si and C?B bond breaking transition states. This vinylidene homologation was used in a short six-step stereoselective synthesis of the proposed structure of machillene, however, synthetic and reported data were found to be inconsistent.
Endo Selectivity in the (4 + 3) Cycloaddition of Oxidopyridinium Ions
Fu, Chencheng,Harmata, Michael,Keto, Angus B.,Krenske, Elizabeth H.,Liu, Jinchu,Regalado, Erik L.,Roseli, Ras Baizureen,Sungnoi, Wanna,Wang, Heather
supporting information, p. 8302 - 8306 (2021/11/01)
The (4 + 3) cycloaddition of 2-trialkylsilyl-4-alkylbutadienes with an N-methyloxidopyridinium ion affords cycloadducts with high regioselectivity and excellent endo selectivity.
COMPOUNDS AND COMPOSITIONS CONTAINING SILICON AND/OR OTHER HETEROATOMS AND/OR METALS AND METHODS OF MAKING AND USING THEM
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Page/Page column 26; 43, (2008/12/05)
The present invention relates to compounds, intermediates, compositions, and methods of making compounds and intermediates related to the compounds of Formula (I) and/or Formula (II) and/or Formula (III) and/or Formula (IV) and/or Formula (VI) and/or Formula (VII) as disclosed herein wherein the various substituents are as defined in the written description.