39491-62-8Relevant articles and documents
Palladium-Catalyzed Regio- A nd Enantioselective Hydrosulfonylation of 1,3-Dienes with Sulfinic Acids: Scope, Mechanism, and Origin of Selectivity
Dong, Dongfang,Zhang, Qinglong,Zi, Weiwei
supporting information, p. 15860 - 15869 (2020/10/18)
Chiral sulfones are important structural motifs in organic synthesis because of their widespread use in pharmaceutical chemistry. In particular, chiral allylic sulfones have drawn particular interest because of their synthetic utility. However, enantioselective synthesis of 1,3-disubstituted unsymmetrical chiral allylic sulfones remains a challenge. In this article, we report a protocol for (R)-DTBM-Segphos/Pd-catalyzed regio- A nd enantioselective hydrosulfonylation of 1,3-dienes with sulfinic acids, which provides atom- A nd step-economical access to 1,3-disubstituted chiral allylic sulfones. The reaction occurs under mild conditions and has a broad substrate scope. Combined experimental and computational studies suggest that the reaction is initiated by a ligand-to-ligand hydrogen transfer followed by a C-S bond reductive elimination via a six-membered transition state. Steric repulsion between the olefinic C-H of the substrate and the tert-butyl group of (R)-DTBM-Segphos was found to be a key factor in the enantiocontrol.
Stereoselective synthesis of 1,3-dienes from propargylic alcohols by LiAlH4/AlCl3
Cui, Dong-Mei,Zhu, Kai,Chen, Li,Qi, Lang-Jun,Zhang, Cheng-Zhu,Zheng, Chen
supporting information, p. 2380 - 2384 (2013/07/26)
Herein we report that LiAlH4/AlCl3 is a very efficient reagent for the reductive dehydration of aryl propargylic alcohols in tetrahydrofuran solvent at reflux to give 1,3-dienes with good yields and high E selection. The reaction con
Rhodium-catalyzed isomerization of unactivated alkynes to 1,3-dienes
Shintani, Ryo,Duan, Wei-Liang,Park, Soyoung,Hayashi, Tamio
, p. 3646 - 3647 (2008/09/20)
A rhodium/binap complex has been found to effectively catalyze the isomerization of unactivated internal alkynes to the corresponding 1,3-dienes in the presence of an azomethine imine as the reaction promoter. The Royal Society of Chemistry 2006.