Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 24, Pages 9997-10004Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo201752y
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Funding
- National Natural Science Foundation of China (NSFC) [21072017, 20732001]
- National Basic Research Program of China [2012CB822100]
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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.
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