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BF3 center dot OEt2-Promoted Diastereoselective Diacetoxylation of Alkenes by PhI(OAc)(2)
Zhong, Wenhe; Yang, Jun; Meng, Xiangbao; Li, Zhongjun
刊名JOURNAL OF ORGANIC CHEMISTRY
2011-12-16
DOI10.1021/jo201752y
76期:24页:9997-10004
收录类别SCI ; IC ; CCR
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Organic
研究领域[WOS]Chemistry
关键词[WOS]HYPERVALENT IODINE(III) REAGENTS ; ACTIVATED IODOSYLBENZENE MONOMER ; CIS-DIHYDROXYLATION ; OXIDATIVE CLEAVAGE ; ASYMMETRIC DIHYDROXYLATION ; SYN-DIHYDROXYLATION ; MOLECULAR-OXYGEN ; EPOXIDATION ; ACID ; EFFICIENT
英文摘要

Selective syn and anti diacetoxylations of alkenes have been achieved using a PhI(OAc)(2)/BF3 center dot OEt2 system in the presence and absence of water, respectively. A broad range of substrates including electron-deficient alkenes (such as alpha,beta-unsaturated esters) could be elaborated efficiently at room temperature with this methodology, furnishing the desired products in good to excellent yields and diastereoselectivity. In particular, a multigram-scale diastereoselective diacetoxylation of methyl cinnamate (5.00 g) was also accomplished in a few hours, maintaining the same efficiency as small-scale reaction. This novel methodology provides an alternative approach for the preparation of various 1,2-diols.

语种英语
WOS记录号WOS:000297715900012
引用统计
被引频次:46[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/66234
专题北京大学药学院_化学生物学系
作者单位Peking Univ, State Key Lab Nat & Biomimet Drugs, Dept Biol Chem, Sch Pharmaceut Sci, Beijing 100191, Peoples R China
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GB/T 7714
Zhong, Wenhe,Yang, Jun,Meng, Xiangbao,et al. BF3 center dot OEt2-Promoted Diastereoselective Diacetoxylation of Alkenes by PhI(OAc)(2)[J]. JOURNAL OF ORGANIC CHEMISTRY,2011,76(24):9997-10004.
APA Zhong, Wenhe,Yang, Jun,Meng, Xiangbao,&Li, Zhongjun.(2011).BF3 center dot OEt2-Promoted Diastereoselective Diacetoxylation of Alkenes by PhI(OAc)(2).JOURNAL OF ORGANIC CHEMISTRY,76(24),9997-10004.
MLA Zhong, Wenhe,et al."BF3 center dot OEt2-Promoted Diastereoselective Diacetoxylation of Alkenes by PhI(OAc)(2)".JOURNAL OF ORGANIC CHEMISTRY 76.24(2011):9997-10004.
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