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DABCO-Catalyzed Coupling of Aldehydes with Activated Double Bonds. 4. Stereoselective Synthesis of Trisubstituted Olefins and Terpenoid Building Blocks via 2-(Hydroksyalkyl)-2-propenoic Esters.
A variety of 2-(hydroksyalkyl)-2-propenoic esters 16a-g has been prepared in high yield by DABCO-catalyzed coupling of aldehydes 14a-g with methyl acrylate.The product esters 16a-g are useful building blocks in syntheses which undergo regioselective and Z-selective SN2 reactions with N-bromosuccinimide/dimethyl sulfide and N-chlorosuccinimide/dimethyl sulfide to furnish (Z)-2-(bromomethyl)-2-alkenoic esters 17a-g and (Z)-2-(chloromethyl)-2-alkenoic esters 18b,c,d, respectively.Similarly, the derived allylic acetates 21g,h, and also allylic bromide 17g react with lithium triethylhydridoborate via mechanism SN2′ to give (E)-2-methyl-2-alkenoic esters 22g,h and respectively, 2-methylenealkanoic esters 20g.Methyl (Z)-6,6-(ethylenedioxy)-2-methyl-2-heptenoate (22h) has been prepared as an intermediate en route to the norsesquiterpenoid ketone 23.The allylic bromides 17d,e,f also furnish (Z)-6-methyl-5-<(trimethylsilyl)methyl>-4-heptene-1,6-diol (19a), (Z)-2-methyl-3-<(trimethylsilyl)methyl>-3-octene-2,7-diol (19e), and (Z)-7-methyl-6-<(trimethylsilyl)methyl>-5-octene-1,2,7-triol (19f), which are terpenoid building blocks.
One of the oldest and most widely used commercial enzyme inhibitors is aspirin, Recommanded Product: 637-64-9, which selectively inhibits one of the enzymes involved in the synthesis of molecules that trigger inflammation. you can also check out more blogs about 637-64-9
Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem