Product stereospecificity in the microbial reductions of hydroaromatic ketones

Kabuto, Kuninobu; Imuta, Mitsuru; Kempner, Ellis S.; Ziffer, Herman

doi:10.1021/jo00406a011

Cited by 49 publications

(14 citation statements)

References 2 publications

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“…For this study, we were required to synthesize a series of related substituted enol acetates 4,6,9,11,13 and 15 (Scheme 3). These enol derivatives were synthesized from the parent phenyl ketones 2,7,8,10,12 amount of p-TsOH or by addition of perchloric acid to a stirred solution of acetic anhydride in carbon tetrachloride 8 to give the required enol acetates 4, 6, 9, 11, 13 and 15, respectively, in good yield (Scheme 3).…”

Section: Resultsmentioning

confidence: 99%

Investigations into theC-deuteriation of enol acetates derived from aryl alkyl ketones

Buksha

Coumbarides

Dingjan

et al. 2005

J Label Compd Radiopharm

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Section: Resultsmentioning

confidence: 99%

Investigations into theC-deuteriation of enol acetates derived from aryl alkyl ketones

Buksha

Coumbarides

Dingjan

et al. 2005

J Label Compd Radiopharm

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“…The organic layer was filtered through a plug of silica and the solvent removed under reduced pressure to leave the product which was purified by column chromatography if necessary. Characterisation data and ee determination methods for reduction products [43][44][45][46][47][48][49][50] are given in the Supporting Information.…”

Section: (S)-n-((1r2r)-12-diphenyl-2-((s)-pyrrolidine-5-carboxamidomentioning

confidence: 99%

Application of Proline‐Functionalised 1,2‐Diphenylethane‐1,2‐diamine (DPEN) in Asymmetric Transfer Hydrogenation of Ketones

Manville

Docherty²,

Padda³

et al. 2011

Eur J Org Chem

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“…expectation that the use of the Misunobu reaction would cleanly invert the configuration at C-1 was based, in part, on results of an earlier study (5) in which we had shown that this reaction on (1 R)-phenylethanol yielded the S-enantiomer with an optical 3b purity of better than 95%.…”

Section: Imentioning

confidence: 99%

Enantioselective ester hydrolyses using Rhizopusnigricans: stereoselective synthesis and absolute stereochemistry of (−)-cis- and (−)-trans-1-hydroxy-4-methyl-1,2,3,4-tetrahydronaphthalene

Kasai¹,

Ziffer²,

Silverton³

1985

Can. J. Chem.

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Enantioselective hydrolysis of racemic acetates of cis-and trans-l-hydroxy-4-methyl-l,2,3,4-tetrahydronaphthalene using Rhizopus nigricans yields chiral alcohols. The absolute stereochemistry of these compounds, and that of a key intermediate in their stereoselective synthesis, r-l-hydroxy-2,t-bromo-4,c-methyl-1,2,3,4-tetrahydronaphthalene, were determined by chemical transformations to I -oxo-4-methyl-l,2,3,4-tetrahydronaphthalene of known absolute stereochemistry. The relative stereochemistry of the acetate of the key intermediate was established by X-ray crystallography.MASAJI KASAI, HERMAN ZIFFER et J. V. SILVERTON. Can. J. Chem. 63, 1287 (1985.L'hydrolyse knantiosklective des acCtates racCmiques des hydroxy-.I mCthyl-4 tetrahydro-1,2,3,4 naphtalenes-cis et trans, effectuke en prksence de Rhizopus nigricans, conduit a des alcools chiraux. On a dktermink la stkrkochimie absolue de ces composCs ainsi que celle d'un intermkdiaire clk dans leur synthiise stCrkosklective, le hydroxy-I-r bromo-2,t mCthyl-4,c tetrahydro-1,2,3,4 naphtalkne, en leur faisant subir des transformations chimiques conduisant a 1'0x0-l mCthyl-4 tktrahydro-1,2,3,4 naphtalene de stCr6ochimie absolue connue. On a dCtermint la stkrkochimie relative de l'acktate de I'intermkdiaire clC en faisant appel i la diffraction des rayons-X.[Traduit par le journal]We recently reported (1) on a method for preparing chiral alcohols of a predictable absolute stereochemistry using the mold, Rhizopus nigricans, by enantioselective hydrolysis of the corresponding racemic acetates. The absolute stereochemistry of the alcohols formed was accounted for by a suggested rule ( l a ) which states that the enantiomer shown in Fig. 1 is the one more rapidly hydrolyzed. The relative sizes of R, and R2 required to account for our results in these hydrolyses are identical to those employed in Horeau's method (2). For example, an aromatic group (R,) is always larger than an alkyl group (R2) and, in cyclic carbinols, a substituted methylene group is larger than an unsubstituted one, etc. This simple concept and the associated empirical observations (1) account for the configurations of some fifty acyclic and cyclic carbinols, several of which required special explanations in order to reconcile their known absolute stereochemistry with data from Horeau's method. Since knowledge of the relative sizes of substituents is critical in predicting the absolute stereochemistry of carbinols formed in these hydrolyses, we needed to establish the influence of distant groups on the relative sizes of substituents on the carbinol carbon. Many data (1 c ) have been collected on 2-substituted 1-acetoxy-l,2,3,4-tetrahydronaphthalenes, and it has been established that a fused benzene ring is effectively larger than a saturated carbon bearing two hydrogens, but smaller than one in which one or both of the hydrogens has been replaced by a chlorine or bromine atom or a methyl or hydroxyl group. In order to examine the influence of distant groups, we have therefore investigated the effects associ...

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Product stereospecificity in the microbial reductions of hydroaromatic ketones

Cited by 49 publications

References 2 publications

Investigations into theC-deuteriation of enol acetates derived from aryl alkyl ketones

Investigations into theC-deuteriation of enol acetates derived from aryl alkyl ketones

Application of Proline‐Functionalised 1,2‐Diphenylethane‐1,2‐diamine (DPEN) in Asymmetric Transfer Hydrogenation of Ketones

Enantioselective ester hydrolyses using Rhizopusnigricans: stereoselective synthesis and absolute stereochemistry of (−)-cis- and (−)-trans-1-hydroxy-4-methyl-1,2,3,4-tetrahydronaphthalene

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