化学
筑地反应
金属化
烷基化
催化作用
对映体
烯丙基重排
立体化学
选择性
药物化学
组合化学
有机化学
作者
Patrick J. Guiry,Therese B. Brennan,Helge Müller‐Bunz
出处
期刊:Synlett
[Georg Thieme Verlag KG]
日期:2022-10-12
卷期号:33 (18): 1841-1846
被引量:2
标识
DOI:10.1055/s-0042-1752342
摘要
Abstract The synthesis of a series of planar chiral P,N-ferrocenylpyrrolidine-containing ligands, with varying substituents at the phosphorus donor atom, is described. The phosphorus donor atom was introduced via a diastereoselective ortho-directed metalation of N-methylpyrrolidinyl ferrocene followed by a quench with various chlorophosphines. These P,N systems are very active in Pd-catalyzed allylic alkylation of 1,3-diphenylpropenyl acetate with dimethylmalonate (conversions of up to 100%) and demonstrated good levels of enantioselectivity (up to 85% ees). Good selectivity for the (R)-enantiomer was observed and mechanistic studies, involving X-ray crystallography and NMR spectroscopic experiments, were employed to help rationalize the observed stereochemical outcome of the reaction.
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