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Cycloalkenyl Halide Substitution Reactions of Enantiopure Arene cis ‐Tetrahydrodiols with Boron, Nitrogen and Phosphorus Nucleophiles
Author(s) -
Boyd D. R.,
Sharma N. D.,
Kaik M.,
Bell M.,
Berberian M. V.,
McIntyre P. B. A.,
Kelly B.,
Hardacre C.,
Stevenson P. J.,
Allen C. C. R.
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100273
Subject(s) - chemistry , enantiopure drug , bromobenzene , nucleophile , boron , iodobenzene , halogen , organic chemistry , halide , phosphorus , nitrogen , substitution reaction , medicinal chemistry , enantioselective synthesis , catalysis , alkyl
Enantiopure arene cis ‐tetrahydrodiols of bromobenzene and iodobenzene have been obtained in good yields, from chemoselective hydrogenation (rhodium‐graphite) of the corresponding cis ‐dihydrodiol metabolites. Palladium‐catalysed substitution of the halogen, by hydrogen, boron, nitrogen and phosphorus nucleophiles, in the acetonide derivatives, has yielded highly functionalised products for application in synthesis with potential as scaffolds for chiral ligands.