79314-57-1Relevant articles and documents
1,3- versus 1,2-Asymmetric Induction in the Reduction of β-Hydroxy Ketones by Intramolecular Hydrosilylation
Anwar, Saeed,Bradley, Gavin,Davis, Anthony P.
, p. 1383 - 1389 (1991)
The role of 1,2-asymmetric induction has been investigated in the 1,3-anti-selective reduction of β-hydroxy ketones via intramolecular hydrosilylation.For the α-methyl β-hydroxy ketones 2a, 3a, the effect of the α-substituent is negligible except that it appears to reinforce 1,3-asymmetric induction.For the α-ethyl β-hydroxy ketones 2b, 3b, 1,3-asymmetric induction is dominant but not overwhelming.The super-acid TfOH2(1+) B(OTf)4(1-) has been used as a catalyst for the hydrosilylation giving, in one case, an improved result when compared with previous methodology.
Synthesis of valuable chiral intermediates by isolated ketoreductases: Application in the synthesis of α-alkyl-β-hydroxy ketones and 1,3-diols
Kalaitzakis, Dimitris,Rozzell, J. David,Smonou, Ioulia,Kambourakis, Spiros
, p. 1958 - 1969 (2007/10/03)
Regio- and stereoselective reductions of α-substituted 1,3-diketones to the corresponding β-keto alcohols or 1,3-diols by using commercially available ketoreductases (KREDs) are described. A number of α-monoalkyl- or dialkyl-substituted symmetrical as well as non-symmetrical diketones were reduced in high optical purities and chemical yields, in one or two enzymatic reduction steps. In most cases, two or even three out of the four possible diastereomers of α-alkyl-β-keto alcohols were synthesized by using different enzymes, and in two examples both ketones were reduced to the 1,3-diol. By replacing the α-alkyl substituent with the OAc group, 1-keto-2,3-diols, as well as 1,2,3-triols were synthesized in high optical purities. These enzymatic reactions provide a simple, highly stereoselective and quantitative method for the synthesis of different diastereomers of valuable chiral synthons from non-chiral, easily accessible 1,3-diketones.
A two-step chemoenzymatic synthesis of the natural pheromone (+)-sitophilure utilizing isolated, NADPH-dependent ketoreductases
Kalaitzakis, Dimitris,Rozzell, J. David,Kambourakis, Spiros,Smonou, Ioulia
, p. 2309 - 2313 (2007/10/03)
Isolated, NADPH-dependent ketoreductases were used for the synthesis of the aggregation pheromone of the pests rice weevil (Sitophilus oryzae L.) and maize weevil (Sitophilus zeamais M.). This is the easiest and most straight forward synthesis of pheromon