Pd-Catalyzed Intramolecular Aminohydroxylation of Alkenes with Hydrogen Peroxide as Oxidant and Water as Nucleophile

被引:113
作者
Zhu, Haitao [1 ]
Chen, Pinhong [1 ]
Liu, Guosheng [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
关键词
C-H BONDS; CIS-AMINOPALLADATION; MOLECULAR-OXYGEN; METHYL-GROUPS; PALLADIUM; OXIDATION; REACTIVITY; AMINOACETOXYLATION; CHLOROAMINATION; HYDROXYLATION;
D O I
10.1021/ja412023b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A palladium-catalyzed intramolecular aminohydroxylation of alkenes was developed, in which H2O2 was applied as the sole oxidant. A variety of related alkyl alcohols could be successfully obtained with good yields and excellent diastereoselectivities, which directly derived from oxidation cleavage of alkyl C-Pd bond by H2O2. Facile transformation of these products provided a powerful tool toward the synthesis of 2-amino-1,3-diols and 3-ol amino acids. Preliminary mechanistic studies revealed that major nucleophilic attack of water (S(N)2 type) at high-valent Pd center contributes to the final C-O(H) bond formation.
引用
收藏
页码:1766 / 1769
页数:4
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