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Catalytic Asymmetric Addition and Telomerization of Butadiene with Enamine Intermediates
CCS Chemistry ( IF 9.4 ) Pub Date : 2021-09-04 , DOI: 10.31635/ccschem.021.202101240
Yaning Wang 1, 2 , Jie Zhang 3 , Chang You 4 , Xueling Mi 3 , Sanzhong Luo 4
Affiliation  

Herein, we report tunable asymmetric addition and telomerization of butadiene by synergistic chiral primary amine/achiral palladium catalysis. A selection of different achiral phosphine ligand in concert with the chiral primary amine-trifluoromethanesulfonic acid (TfOH) conjugates enables both chemo- and enantioselective control of the coupling with butadiene. Bidentate [(oxydi-2,1-phenylene)-bis-(diphenylphosphine)] (DPEPhos) ligand led to 1,4-addition adduct whereas monodentate (p-Tol)3P ligand gave the telomerization product. A range of α-branched β-ketoesters and aldehydes could be applied to afford allylation or telomerization products bearing all-carbon quaternary centers at high efficiency and good chemo-, regio-, and stereoselectivities.



中文翻译:

丁二烯与烯胺中间体的催化不对称加成和调聚反应

在此,我们报告了通过协同手性伯胺/手性钯催化进行丁二烯的可调不对称加成和调聚。选择不同的非手性膦配体与手性伯胺-三氟甲磺酸 (TfOH) 偶联物​​相结合,可以对与丁二烯的偶联进行化学和对映选择性控制。双齿 [(oxydi-2,1-phenylene)-bis-(diphenylphosphine)] (DPEPhos) 配体产生 1,4-加成物,而单齿 (p-Tol) 3 P 配体产生调聚产物。一系列α-支链β-酮酯和醛可用于以高效和良好的化学选择性、区域选择性和立体选择性提供带有全碳季铵中心的烯丙基化或调聚产物。

更新日期:2021-09-06
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