Enzymatic and chemoenzymatic: synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes
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 0300-922XFull text not available from this repository.
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|
|Date:||21 June 1998|
|Number of Pages:||9|
|Page Range:||pp. 1935-1943|
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