Regio- and Stereoselective Addition of HO/OOH to Allylic Alcohols

被引：7
|
作者：
Wang, Xiao-Tao [1 ,2 ]
Han, Wei-Bo [1 ,2 ]
Chen, Hui-Jun [1 ,2 ]
Zha, Qinghong [1 ,2 ]
Wu, Yikang [1 ,2 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
[2] Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai 200032, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 15期
基金：
中国国家自然科学基金;
关键词：
ASYMMETRIC-SYNTHESIS; HOMOALLYLIC ALCOHOLS; REARRANGEMENT; PERHYDROLYSIS; EPOXIDATION; OXETANES; KETONES; HYDROPEROXIDES; ALKYLATION; OXIRANES;
D O I：
10.1021/acs.joc.0c01280
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A range of allylic alcohols are shown to readily react with ethereal H2O2 in the presence of catalytic amounts of Na2MoO4-gly or MoO2(acac)(2), affording the C=C trans hydroxylation-hydroperoxylation products in good yields with high regio- and stereoselectivity. Use of enantiomers of cyclic substrates resulted in corresponding enantiopure diol-tert-hydroperoxides. The possibility of further conversion of the diol-tert-hydroperoxides into triols or linear building blocks with an isolated tert-peroxy group containing a quaternary center is also exemplified.
引用
收藏
页码：10007 / 10021
页数：15
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