Hypervalent iodine-mediated Ritter-type amidation of terminal alkenes: The synthesis of isoxazoline and pyrazoline cores

• Sang Won Park,
• Soong-Hyun Kim,
• Jaeyoung Song,
• Ga Young Park,
• Darong Kim,
• Tae-Gyu Nam and
• Ki Bum Hong

Beilstein J. Org. Chem. 2018, 14, 1028–1033, doi:10.3762/bjoc.14.89

• alkene functionalization utilizing a PhI(OAc)2 ((diacetoxyiodo)benzene, PIDA)/Lewis acid combination in order to access isoxazoline and pyrazoline cores. Based on allyl ketone oximes and allyl ketone tosylhydrazones, we have developed an alkene oxyamidation and amido-amidation protocol en route to

• . Keywords: amido-amidation; hypervalent iodine; isoxazoline; metal-free; oxyamidation; pyrazoline; Introduction Isoxazoline and pyrazoline-containing heterocycles are abundant in natural products and biologically active molecules [1][2][3][4][5]. Thus, these scaffolds are also important from the standpoint

• , this hypervalent iodine-mediated Ritter-type oxyamidation of 1a proved less efficient in the presence of solvent combinations with acetonitrile, despite acetonitrile being used in vast excess (see Supporting Information File 1, Table S1). Herein, we entail the first example of a hypervalent iodine(III

Difunctionalization of alkenes with iodine and tert-butyl hydroperoxide (TBHP) at room temperature for the synthesis of 1-(tert-butylperoxy)-2-iodoethanes

• Hao Wang,
• Cui Chen,
• Weibing Liu and
• Zhibo Zhu

Beilstein J. Org. Chem. 2017, 13, 2023–2027, doi:10.3762/bjoc.13.200

• dioxygenation [10][11], dihydroxylation [10][12], bisperoxidation [13], oxyamidation [14], aminohydroxylation [15], oxyphosphorylation [16], deamination [17] and carbonylation–peroxidation [18]. Several very recent reports have pertained to metal-free catalysts for difunctionalization of alkenes such as UV

Study on the total synthesis of velbanamine: Chemoselective dioxygenation of alkenes with PIFA via a stop-and-flow strategy

• Huili Liu,
• Kuan Zheng,
• Xiang Lu,
• Xiaoxia Wang and
• Ran Hong

Beilstein J. Org. Chem. 2013, 9, 983–990, doi:10.3762/bjoc.9.113

• Recently, Tellitu, Dominguez, and co-workers reported an intramolecular oxyamidation of alkene 11 with phenyliodine(III)-bis(trifluoroacetate) (PIFA) (Scheme 3) [46]. The lactam 12 was originally assigned as an unstable intermediate, which should be subsequently reduced to pyrrolidine 13. It was

• . X-ray analysis further contributed to the elucidation of the linear structure of 13 as shown in Scheme 5 [49]. The revised structure 13 implies that the amide 11 did not undergo the oxyamidation under the previously defined reaction conditions. Alternatively, it appears that iodolactonization of the

• enantioselective desymmetrization are currently pursued in our laboratory and will be reported in due course. Hydrolysis of iminolactone 18 under basic conditions. Biogenetic origin of Vinca alkaloids. Synthetic strategy for velbanamine based on chemoselective dioxygenation. Intramolecular oxyamidation of alkene