%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