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DOI: 10.1039/A800809D (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1998, 1935-1944

Enzymatic and chemoenzymatic synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes

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Derek R. Boyd, Narain D. Sharma, Breige Byrne, Mark V. Hand, John F. Malone, Gary N. Sheldrake, John Blacker and Howard Dalton

Abstract

Toluene dioxygenase-catalysed oxidation of mono-substituted benzene substrates (R = F, Cl, Br, I, Me, Et, CH2OAc, CH[double bond, length half m-dash]CH2, C[triple bond, length half m-dash]CH, 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[hair space])-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[double bond, length half m-dash]CH2, Bun, 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 1H 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.

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