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Enzymatic and chemoenzymatic: synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes
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UNSPECIFIED (1998) Enzymatic and chemoenzymatic: synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 (12). pp. 1935-1943. ISSN 0300-922X
Full text not available from this repository.Abstract
Toluene dioxygenase-catalysed oxidation of mono-substituted benzene substrates (R = F, Cl, Br, I, Me, Et, CH2OAc, CH=CH2, C=H, CF3, CN, OMe, OEt, SMe) in growing cultures of Pseudomonas putida UV4 yielded the corresponding cis-dihydrodiol metabolites. Palladium-catalysed cross-coupling of cis-(1S,2S)-1,2-dihydroxy-3-iodocyclohexa-3,5-diene with a range of tributyltin compounds provided a chemoenzymatic route to a further series of cis-dihydrodiol derivatives of monosubstituted benzenes (R = D, CH2CH=CH2, Bu-n, SEt, SPri, SBut, SPh, SC6H4Me-4). The enantiopurities and absolute configurations of the cis-dihydrodiols, obtained by both enzymatic and chemoenzymatic routes, were determined by several new:methods including H-1 NMR spectroscopic analysis of the bis-MTPA esters of the 4-phenyl-1,2,4-triazoline-3,5-dione cycloadducts, X-ray crystallography, circular dichroism spectroscopy and stereochemical correlation.
| Item Type: | Journal Article |
|---|---|
| Subjects: | Q Science > QD Chemistry |
| Journal or Publication Title: | JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 |
| Publisher: | ROYAL SOC CHEMISTRY |
| ISSN: | 0300-922X |
| Date: | 21 June 1998 |
| Number: | 12 |
| Number of Pages: | 9 |
| Page Range: | pp. 1935-1943 |
| Publication Status: | Published |
| URI: | http://wrap.warwick.ac.uk/id/eprint/15589 |
Data sourced from Thomson Reuters' Web of Knowledge
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