Registro:

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• Though the difference in yields between the entries 12 and 13 is not significant, the choice of PhI(OPiv)2 as the oxidant to study the scope of the reaction was motivated by the reaction of alkene 1i with PhI(OAc)2 that leads to the expected epoxide 2i in only 40 % yield [70 % with PhI(OPiv)2; see Table]; The reaction with a tetrasubstituted alkene only leads to the recovery of the starting material; An allylic alcohol such as geraniol does not afford the corresponding epoxide under the reaction conditions. A complex mixture of products, instead, is obtained as indicated by the, H NMR of the crude; In order to circumvent the lack of reactivity of α,β-unsaturated ketones, these were converted to cyclic ketals. However, application of the reaction conditions to the latter only leads to the starting ketone following cleavage of the ketal; It is worth mentioning that the reaction of m-CPBA with the ortho-cyano styrene only leads to the corresponding epoxide 2s in 13 % yield. See: “ACC inhibitors and uses thereof”, PCT/ WO 2013071169A1, May 16, 2013; Miyamoto, K., Tada, N., Ochiai, M., (2007) J. Am. Chem. Soc., 129, p. 2772
• Use of other Lewis acids such as Cu(OTf)2, Pd(OAc)2, BF3·OEt2, Sc(OTf)3, CeCl3, LiCl, or TMSOTf, in the epoxidation of 1i leads to either its decomposition or the formation of the expected product 2i in very low yield; Yang, Y., Diederich, F., Valentine, J.S., (1991) J. Am. Chem. Soc., 113, p. 7195. , For a previous Lewis acid-catalyzed olefin epoxidation with an iodine(III) oxidant, see
• The electron-withdrawing property of the ligand on the dirhodium complex would allow for tuning its Lewis acidity. The latter should be Lewis acidic enough for the activation of the hypervalent iodine reagent, however, a too strong Lewis acid is likely to increase its oxidizing character thereby inducing the decomposition of the resulting epoxide, as demonstrated by the study of Ochiai (see ref. 21); Zhang, J., Szabo, K.J., Himo, F., (2017) ACS Catal., 7, p. 1093. , It should be mentioned that a recent theoretical study supports a metathesis mechanism for the functionalization of alkenes using a hypervalent fluoroiodine reagent
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