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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.
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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 | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Journal or Publication Title: | JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | ||||
Publisher: | ROYAL SOC CHEMISTRY | ||||
ISSN: | 0300-922X | ||||
Official Date: | 21 June 1998 | ||||
Dates: |
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Number: | 12 | ||||
Number of Pages: | 9 | ||||
Page Range: | pp. 1935-1943 | ||||
Publication Status: | Published |
Data sourced from Thomson Reuters' Web of Knowledge
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