Organic synthesis utilizing chiral sulfoxides.
نویسندگان
چکیده
منابع مشابه
Application of chiral sulfoxides in asymmetric synthesis
Over the last three decades, the sulfinyl group has received considerable attention in asymmetric synthesis1‒5 as a chiral tool. The sulfinyl group is widely used as to bring about numerous asymmetric transformations. The effectiveness of the sulfoxide in diastereoselective auxiliary-induced reactions is mainly due to the steric and stereo electronic differences existing between the substituent...
متن کاملProtein engineering of toluene monooxygenases for synthesis of chiral sulfoxides.
Enantiopure sulfoxides are valuable asymmetric starting materials and are important chiral auxiliaries in organic synthesis. Toluene monooxygenases (TMOs) have been shown previously to catalyze regioselective hydroxylation of substituted benzenes and phenols. Here we show that TMOs are also capable of performing enantioselective oxidation reactions of aromatic sulfides. Mutagenesis of position ...
متن کاملProtein engineering of nirobenzene dioxygenase for enantioselective synthesis of chiral sulfoxides.
Nitrobenzene dioxygenase (NBDO) from Comamonas sp. is shown here to perform enantioselective oxidation of aromatic sulfides. Several para-substituted alkyl aryl sulfides were examined and it was found that the activity of the enzyme is dependent on the size of the substrate. Saturation mutagenesis was performed on different residues in the active site in order to improve activity and selectivit...
متن کاملOn the synthesis of α-amino sulfoxides.
A synthetic study on the preparation of N-Boc α-amino sulfoxides has revealed an unexpected instability which is believed to be due to α-elimination of the sulfoxide to give an iminium ion. Full synthetic details are reported on two main synthetic routes: lithiation and sulfinate trapping of N-Boc heterocycles and oxidation of N-Boc α-amino sulfides. Six novel α-amino sulfoxides were successful...
متن کاملEnantioseparation of chiral sulfoxides and sulfinate esters by capillary electrophoresis.
Forty-one chiral sulfoxides and sulfinate esters were separated using sulfated beta-cyclodextrin and carboxymethyl beta-cyclodextrin as chiral selectors. Binding constants of some analytes to both chiral selectors were measured in order to examine and help explain the observed migration behavior and enantioselectivity trends. Overall, sulfated beta-cyclodextrin separated a greater number of com...
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ژورنال
عنوان ژورنال: Journal of Synthetic Organic Chemistry, Japan
سال: 1986
ISSN: 0037-9980,1883-6526
DOI: 10.5059/yukigoseikyokaishi.44.576