82167-69-9Relevant academic research and scientific papers
Tetramethyleneethane Equivalents: Recursive Reagents for Serialized Cycloadditions
Wender, Paul A.,Jeffreys, Matthew S.,Raub, Andrew G.
, p. 9088 - 9093 (2015/08/03)
New reactions and reagents that allow for multiple bond-forming events per synthetic operation are required to achieve structural complexity and thus value with step-, time-, cost-, and waste-economy. Here we report a new class of reagents that function like tetramethyleneethane (TME), allowing for back-to-back [4 + 2] cycloadditions, thereby amplifying the complexity-increasing benefits of Diels-Alder and metal-catalyzed cycloadditions. The parent recursive reagent, 2,3-dimethylene-4-trimethylsilylbutan-1-ol (DMTB), is readily available from the metathesis of ethylene and THP-protected 4-trimethylsilylbutyn-1-ol. DMTB and related reagents engage diverse dienophiles in an initial Diels-Alder or metal-catalyzed [4 + 2] cycloaddition, triggering a subsequent vinylogous Peterson elimination that recursively generates a new diene for a second cycloaddition. Overall, this multicomponent catalytic cascade produces in one operation carbo- and heterobicyclic building blocks for the synthesis of a variety of natural products, therapeutic leads, imaging agents, and materials. Its application to the three step synthesis of a new solvatochromic fluorophore, N-ethyl(6-N,N-dimethylaminoanthracene-2,3-dicarboximide) (6-DMA), and the photophysical characterization of this fluorophore are described. (Chemical Equation Presented).
2-DIMETHYLAMINOMETHYL-3-TRIMETHYLSILYLMETHYL-1,3-BUTADIENE AS 2,2'-BIALLYL DIRADICAL SYNTHON. A NEW AND FACILE ENTRY TO 1,2-DIMETHYLENECYCLOHEXANES, AND AND RING SYSTEMS
Hosomi, Akira,Otaka, Ken,Sakurai, Hideki
, p. 2881 - 2884 (2007/10/02)
The title compound, prepared readily by the cross-coupling reaction of β-bromoallyltrimethylsilane and the Grignard reagent from β-bromoallyldimethylamine, is an effective reagent as 2,2'-biallyl diradical synthon to give and 6.7) ring systems by t
