Palladium-Catalyzed Asymmetric Decarboxylative [4+2] Dipolar Cycloaddition of 4-Vinyl-1,3-dioxan-2-ones with α,β-Disubstituted Nitroalkenes Enabled by a Benzylic Substituted P,N-Ligand

被引：30
|
作者：
Du, Juan [2 ]
Hua, Yuan-Da [2 ]
Jiang, Yang-Jie [2 ]
Huang, Shuai [2 ]
Chen, Di [2 ]
Ding, Chang-Hua [1 ]
Hou, Xue-Long [2 ,3 ]
机构：
[1] Shanghai Univ, Innovat Drug Res Ctr, Dept Chem, Shanghai 200444, Peoples R China
[2] Chinese Acad Sci, Ctr Excellence Mol Synth, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, Shanghai 200032, Peoples R China
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 14期
基金：
中国国家自然科学基金;
关键词：
CONCISE SYNTHESIS; CONSTRUCTION; VINYL; BENZOXAZINONES; DERIVATIVES; CARBONATES; LIGANDS;
D O I：
10.1021/acs.orglett.0c01638
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Pd-catalyzed asymmetric [4+2] cycloaddition reaction of an aliphatic 1,4-dipole with singly activated electron-deficient alkenes is realized for the first time, enabled by using a newly developed benzylic substituted P,N-ligand, affording tetrahydropyrans having three continuous chiral centers in high yields with high diastereo- and enantioselectivities. The rational transition states of the reaction as well as the role of the benzylic chiral center are proposed.
引用
收藏
页码：5375 / 5379
页数：5
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