Cycloalkenyl Halide Substitution Reactions of Enantiopure Arene cis-Tetrahydrodiols with Boron, Nitrogen and Phosphorus Nucleophiles

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...

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Veröffentlicht in:	Advanced synthesis & catalysis 2011-09, Vol.353 (13), p.2455-2465
Hauptverfasser:	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.
Format:	Artikel
Sprache:	eng
Schlagworte:	Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology Boron catalytic hydrogenation Chemistry chemoenzymatic synthesis cis-dihydrodiols cis-tetrahydrodiols Derivatives Exact sciences and technology Fundamental and applied biological sciences. Psychology Halogens Hydrogenation Ligands Methods. Procedures. Technologies Nucleophiles Organic chemistry Organometalloidal and organometallic compounds P derivatives Phosphorus Preparations and properties Synthesis
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Beschreibung
Zusammenfassung:	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.
ISSN:	1615-4150 1615-4169 1615-4169
DOI:	10.1002/adsc.201100273