170211-25-3Relevant academic research and scientific papers
Stereoselective cis-dihydroxylation of azulene and related non-aromatic polyenes
Bowers, Nigel I.,Boyd, Derek R.,Sharma, Narain D.,Kennedy, Martina A.,Sheldrake, Gary N.,Dalton, Howard
, p. 1831 - 1834 (1998)
Dioxygenase-catalysed dihydroxylation of azulene and related non- aromatic polyenes has been found to yield enantiopure chiral cis-diols of synthetic potential.
Regiodivergent reactions through catalytic enantioselective silylation of chiral diols. Synthesis of sapinofuranone A
Rodrigo, Jason M.,Zhao, Yu,Hoveyda, Amir H.,Snapper, Marc L.
scheme or table, p. 3778 - 3781 (2011/10/01)
Through the use of an amino acid based imidazole catalyst, a regiodivergent silylation of chiral diols in cases where there is not a significant steric and electronic difference between the regioisotopic hydroxyl groups has been developed. This transformation allows for the conversion of racemic diols into regioisomeric, enantiomerically enriched, monosilylated products. The utility of this process is highlighted in the efficient enantioselective preparation of a useful synthetic intermediate and the natural product, sapinofuranone A.
Cycloalkenyl halide substitution reactions of enantiopure arene cis-tetrahydrodiols with boron, nitrogen and phosphorus nucleophiles
Boyd,Sharma,Kaik,Bell,Berberian,McIntyre,Kelly,Hardacre,Stevenson,Allen
scheme or table, p. 2455 - 2465 (2011/11/04)
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. Copyright
Desymmetrization of hydrazinocyclohexadienes: A new approach for the synthesis of polyhydroxylated aminocyclohexanes
Errastl, Gauthier,Kounde, Cyrille,Mlrguet, Olivier,Lecourt, Thomas,Micouln, Laurent
supporting information; experimental part, p. 2912 - 2915 (2009/12/06)
Hydrazlnocyclohexadlenes, easily prepared by an ene-reactlon between commercially available azodlcarboxylate reagents and cyclohexadlene, are Interesting substrates for desymmetrlzatlon reactions. Under Sharpless asymmetric dihydroxylation conditions, the
Biocatalytic asymmetric dihydroxylation of conjugated mono-and poly-alkenes to yield enantiopure cyclic cis-diols
Boyd, Derek R.,Sharma, Narain D.,Bowers, Nigel I.,Brannigan, Ian N.,Groocock, Melanie R.,Malone, John F.,McConville, Gareth,Allen, Christopher C. R.
, p. 1081 - 1089 (2007/10/03)
Dioxygenase-catalysed asymmetric dihydroxylation, of a series of conjugated monoalkenes and polyenes, was found to yield the corresponding monols and 1,2-dihydrodiols. The diol metabolites were obtained from monosubstituted, gem-disubstituted, cis-disubstituted, and trisubstituted alkene substrates, using whole cells of Pseudomonas putida strains containing toluene and naphthalene dioxygenases. Dioxygenase selection and alkene type were established as important factors, in the preference for dioxygenase-catalysed 1,2-dihydroxylation of conjugated alkene or arene groups, and monohydroxylation at benzylic or allylic centres. Competition from allylic hydroxylation of methyl groups was observed only when naphthalene dioxygenase was used as biocatalyst. The structures, enantiomeric excess values and absolute configurations of the bioproducts, were determined by a combination of stereochemical correlation, spectroscopy (NMR and CD) and X-ray diffraction methods. cis-1,2-Diol metabolites from arenes, cyclic alkenes and dienes were generally observed to be enantiopure (> 98% ee), while 1,2-diols from acyclic alkenes had lower enantiomeric excess values (2-symmetrical ketone.
