%0 Generic %A L. García Ruano, José %A Fernández-Ibáñez, M. Ángeles %A Maestro, M. Carmen %D 2006 %T Efficient trans-Selectivity in the Cyclocondensation of (S)-2-[2-(p-Tolylsulfinyl)phenyl]acetaldehyde with Activated Dienes Catalyzed by Yb(OTf)3 %U 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 %R 10.1021/jo061128n.s001 %2 https://acs.figshare.com/ndownloader/files/4762540 %K adduct %K carbonyl grouping %K presence %K Efficient %K diene %K Raney Ni %K sulfinyl %K Activated Dienes Catalyzed %K Yb %K mechanism %K intermediate %K induction %K Cyclocondensation %K stereoselective manner %K Danishefsky %K isolation %K cleavage %K bond %K dihydro %X Reactions of (S)-2-[2-(p-tolylsulfinyl)phenyl]acetaldehyde 1 with Danishefsky's and related dienes took place in the presence of Yb(OTf)3 in a completely stereoselective manner, mediated by a remote sulfinyl group (1,5-asymmetric induction), to afford the corresponding 2,3-dihydro-4H-pyran-4-ones. These reactions followed a stepwise mechanism, as was corroborated by isolation of the corresponding intermediates, with a high level of trans-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. %I ACS Publications