L. García Ruano, José Fernández-Ibáñez, M. Ángeles Maestro, M. Carmen Efficient <i>trans</i>-Selectivity in the Cyclocondensation of (<i>S</i>)-2-[2-(<i>p</i>-Tolylsulfinyl)phenyl]acetaldehyde with Activated Dienes Catalyzed by Yb(OTf)<sub>3</sub> Reactions of (<i>S</i>)-2-[2-(<i>p</i>-tolylsulfinyl)phenyl]acetaldehyde <b>1 </b>with Danishefsky's and related dienes took place in the presence of Yb(OTf)<sub>3</sub> in a completely stereoselective manner, mediated by a remote sulfinyl group (1,5-asymmetric induction), to afford the corresponding 2,3-dihydro-4<i>H</i>-pyran-4-ones. These reactions followed a stepwise mechanism, as was corroborated by isolation of the corresponding intermediates, with a high level of <i>trans</i>-selectivity for 4-methyl-substituted dienes. Treatment of the adducts with Raney Ni provided concomitant cleavage of the C−S bond and reduction of the conjugated carbonyl grouping. adduct;carbonyl grouping;presence;Efficient;diene;Raney Ni;sulfinyl;Activated Dienes Catalyzed;Yb;mechanism;intermediate;induction;Cyclocondensation;stereoselective manner;Danishefsky;isolation;cleavage;bond;dihydro 2006-09-29
    https://acs.figshare.com/articles/dataset/Efficient_i_trans_i_Selectivity_in_the_Cyclocondensation_of_i_S_i_2_2_i_p_i_Tolylsulfinyl_phenyl_acetaldehyde_with_Activated_Dienes_Catalyzed_by_Yb_OTf_sub_3_sub_/3056791
10.1021/jo061128n.s001