Stereospecific and stereoselective reactions. I. Preparation of amines from alcohols

Reduction and Preparation of a Phthalimide Derivative from a Furo-heliangolide

“…Several phthalimide derivatives are known to be active against Tripanosoma cruzi [5]; as Mitsunobu [6,7] has described a general method for transforming alcohols into phthalimide derivatives under reasonably mild conditions, we decided to apply this method to goyazensolide. The reaction is very simple, consisting only in mixing the reagents in THF and stirring at room temperature for several hours; separation and purification of the product was not as easy because some excess reagents and by-products have R f values similar to the R f of the product, rendering the purification a rather laborious process.…”

Synthesis and pharmacological characterization of new tetrahydrofuran based compounds as conformationally constrained histamine receptor ligands

“…The hydroxy group was converted into a phthalimide moiety via a Mitsunobu reaction. 28 In comparison to the similar transformation of 26a to 27a described above, the reaction proceeded with the formation of smaller amounts of ring opening products and this with higher yield to the desired 35 (55% vs. 29% for 27a) for reasons that are not clear. Hydrazinolysis gave rise to the amine 9a.…”

“…To displace the hydroxyl group of the (3R)-isomer 26a with an amino moiety, a phthaloylimination under Mitsunobu conditions and subsequent hydrazinolysis were performed. 28 By treating 26a with phthalimide in the presence of PPh 3 and DIAD, the desired phthalimide 27a was obtained in low yield. Further ring-opening gave phthalimides 28 as a mixture of epimers due to a cyclopropylcarbinyl-homoallylic rearrangement (Scheme 4).…”

Photo‐Crosslinked Side‐Chain Liquid‐Crystalline Elastomers for Microsystems

“…[7][8][9] The benzophenone derivative (SCPC) was obtained using Mitsubonu conditions. [10,11] In a 250 mL round-bottomed flask, 10.0 g (50 mmol) of 4-hidroxybenzophenone, and 14.6 g (56 mmol) of triphenylphosphine (PPh 3 ) were placed, and 50 mL of anhydrous THF were added. The system was magnetically stirred and purged with nitrogen for 15 min.…”