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J Org Chem. 2014 Jul 18;79(14):6688-94. doi: 10.1021/jo501178k. Epub 2014 Jul 3.

Asymmetric epoxidation of olefins with hydrogen peroxide by an in situ-formed manganese complex.

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  • 1Dalian Institute of Chemical Physics, Chinese Academy of Sciences , Dalian 116023, People's Republic of China.

Abstract

Asymmetric epoxidation of a variety of cis, trans, terminal, and trisubstituted olefins in excellent yields (up to 94%) and enantioselectivities (>99% ee) by an in situ-formed manganese complex using H2O2 has been developed. A relationship between the hydrophobicity of the catalyst imposed by ligand and the catalytic activity has been observed. The influence of the amount and identity of the acid additive was examined, and improved enantioselectivities were achieved through the use of a catalytic amount of a carboxylic acid additive.

PMID:
24969226
[PubMed - indexed for MEDLINE]
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