Brønsted Acid‐Catalyzed Dihydroxylation of Olefins in Aqueous Medium

Abstract

Abstract:The trans-dihydroxylation of olefins occurs efficiently by aqueous hydrogen peroxide catalyzed by p-toluenesulfonic acid at 50 8C, allowing the catalyst reuse and an outstanding substrate functional group tolerance such as tert-butoxycarbonylamino (BocNH), benzyloxycarbonylamino (CbzNH), benzyloxy (OBn), tosyloxy (OTs), hindered ketal, (2-trimethylsilyl)ethoxymethoxy (OSEM), benzylamino (NBz), benzyloxy (OBz) and free amino acid.

Magnetically separable and reusable rGO/Fe3O4 nanocomposites for the selective liquid phase oxidation of cyclohexene to 1,2-cyclohexane diol

“…[20][21][22] The H 2 O 2 assisted cyclohexene oxidation to 1,2-diol in a catalytic route has been also reported over a set of homogeneous and heterogeneous catalysts. [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] For example, Usui et al 26 reported a maximum diol yield of 98% in a solvent-and metal-free cyclohexene oxidation using H 2 O 2 , catalyzed by immobilized sulfonic acids. In another work, Rosatella et al 27 reported the application of Brønsted acids in the catalytic conversion of cyclohexene to diol.…”

Recognition of a Bromide Ion by the Protonated Form of 2‐(1H‐Imidazol‐2‐ylthio)‐3‐methylnaphthalene‐1,4‐dione

“…When we tested substrate 10 a , which has a labile aldehyde group, we were pleased to find that target molecule substrate 11 a was also cleaved smoothly under green light irradiation to give desired ( S )‐1‐phenylethanol 11 b with only slightly diminished ee (entry 10). We found that alkenes fell outside the substrate scope of the protocol, owing to the known acid‐catalyzed dihydroxylation of the double bond 22. However, the terminal alkyne of substrate 12 a was compatible with the protocol, and corresponding alcohol 12 b was obtained in moderate yield (entry 11).…”

A Review of the Pharmacological Activities and Recent Synthetic Advances of γ-Butyrolactones

“…The cascade epoxidation of olefin 1 with peracetic acid and an intramolecular epoxide opening reaction provided γ -butyrolactone 2 . TfOH was proposed as a catalyst in both the ring-opening reaction via epoxide activation and acetylation of the subsequent hydroxyl group of γ -butyrolactone [ 74 ]. This method was applied to intramolecular lactonization as well as the intermolecular diacetylation of olefins.…”