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

页码：10007 / 10021

页数：15

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