A route to 1,2-diols by enantioselective organocatalytic α-oxidation with molecular oxygen

被引:58
作者
Ibrahem, Ismail [1 ]
Zhao, Gui-Ling [1 ]
Sunden, Henrik [1 ]
Cordova, Armando [1 ]
机构
[1] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
基金
瑞典研究理事会;
关键词
D O I
10.1016/j.tetlet.2006.04.133
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A route to 1,2-diols by the direct organocatalytic enantioselective alpha-oxidation of aldehydes using molecular oxygen is presented. Protected commercially available chiral pyrrolidines catalyze the asymmetric alpha-oxidation of aldehydes with singlet molecular oxygen with high enantioselectivity to furnish the corresponding diols after in situ reduction in high yield with up to 98% ee. Electrophilic singlet molecular oxygen was photo or chemically generated ('dark' O-1(2)). (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4659 / 4663
页数:5
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