The synthesis of chiral β-aryl-α,β-unsaturated amino alcohols via a Pd-catalyzed asymmetric allylic amination

被引:38
|
作者
Quan, Mao [1 ]
Butt, Nicholas [1 ]
Shen, Jiefeng [2 ]
Shen, Kaiji [2 ]
Liu, Delong [2 ]
Zhang, Wanbin [1 ,2 ]
机构
[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China
[2] Shanghai Jiao Tong Univ, Sch Pharm, Shanghai 200240, Peoples R China
关键词
1ST TOTAL-SYNTHESIS; DIPHOSPHINE LIGANDS; EFFICIENT; ALKYLATION; ALLYLATION; FERROCENE; IMINES; ROUTE;
D O I
10.1039/c3ob41642a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral beta-aryl-alpha,beta-unsaturated amino alcohols were synthesized via a Pd-catalyzed asymmetric allylic amination of 4-aryl-1,3-dioxolan-2-one using planar chiral 1,2-disubstituted ferrocene-based phosphinooxazolines as ligands. Under the optimized reaction conditions, a series of substrates were examined and the products were obtained in good to excellent yields (up to 92%) and enantioselectivities (up to 98% ee) under mild reaction conditions. The desired products were determined to be of (R)-configuration and could subsequently be transformed into compounds with interesting biological activity using simple transformations.
引用
收藏
页码:7412 / 7419
页数:8
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