Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 29, Pages 5642-5649Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201000733
Keywords
Phosphorus; Phosphanes; Asymmetric synthesis; Stereoselectivity; Oxidation; Substituent effects
Categories
Funding
- Science Foundation Ireland (SFI) [RFP/06/CH0013, RFP/08/CHE1251]
- UCD Centre for Synthesis and Chemical Biology (CSCB)
- University College Dublin
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The effects of aryl ring substitution on the dynamic resolution of aryl(methyl)phenylphosphanes under asymmetric Appel reaction conditions have been studied. As expected, substitution at the ortho position strongly affects the degree of stereoselection that can be achieved. Unexpectedly, however, there was no variation of stereoselectivity with the electronic nature of the para substituents, which suggests that there are two selection processes in operation. An unusual halogen-exchange process was observed in the arylphenylphosphinous chlorides on route to the required tertiary phosphane substrates.
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