Synthesis of Tetrahydrofurans by Cyclization of Homoallylic Alcohols with Iodine/Iodine(III)
作者:Ramon S. Vasconcelos、Luiz F. Silva、Athanassios Giannis
DOI:10.1021/jo102413u
日期:2011.3.4
Tetrahydrofuran derivatives can be obtained by cyclofunctionalization of homoallylic alcohols bearing a terminal double bound by using [hydroxy(tosyloxy)iodo]benzene (HTIB, Koser’s reagent) in the presence of a catalytic amount of I2 (20 mol %) in MeOH under mild conditions. This transformation is an overall 5-endo-trig cyclization, which occurs by two different pathways. The first is a 4-exo-trig
四氢呋喃衍生物可通过在催化量的I 2(20 mol%)在MeOH中的存在下,在催化量的I 2(20 mol%)存在下,通过使用[羟基(甲苯磺酰氧基)碘]苯(HTIB,Koser's试剂)对带有末端双键的带有末端双键的均烯丙基醇进行环官能化而获得情况。该转化是总体的5-内-trig环化,其通过两种不同的途径发生。第一个是4- exo - trig环化,然后是环扩环,而第二个是亲电加成,然后是5- endo - tet环化。