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P ‐Stereogenic Phosphorus Compounds: Effect of Aryl Substituents on the Oxidation of Arylmethylphenylphosphanes under Asymmetric Appel Conditions
Author(s) -
Rajendran Kamalraj V.,
Kennedy Lorna,
Gilheany Declan G.
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000733
Subject(s) - chemistry , stereocenter , aryl , ring (chemistry) , stereoselectivity , halogen , stereochemistry , medicinal chemistry , substitution (logic) , enantioselective synthesis , organic chemistry , catalysis , alkyl , computer science , programming language
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 ofstereoselection 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.