Dual-Ligand-Enabled Ir(III)-Catalyzed Enantioselective C–H Amidation for the Synthesis of Chiral Sulfoxides

ACS Catalysis ◽  
2020 ◽  
Vol 10 (13) ◽  
pp. 7207-7215 ◽  
Author(s):  
Wentan Liu ◽  
Wu Yang ◽  
Jiefeng Zhu ◽  
Yonghong Guo ◽  
Na Wang ◽  
...  
Keyword(s):  
Chiral Sulfoxides

Chemistry of Fenchonesulfonic Acid Derivatives

1995 ◽  
Vol 50 (2) ◽  
pp. 283-288 ◽  
Author(s):  
Gabriele Wagner ◽  
Uwe Verfürth ◽  
Rudolf Herrmann
Keyword(s):  
Acetic Anhydride ◽  
Thionyl Chloride ◽  
Sulfonic Acid ◽  
Reaction Rate ◽  
Enantiomeric Excess ◽  
Methyl Group ◽  
Close Analogy ◽  
Chiral Sulfoxides ◽  
Mndo Calculations ◽  
Nmr Techniques

(1 S) - (+)-Fenchone is sulfonated by SO3 or H2SO4/acetic anhydride in the bridgehead methyl group. This could be confirmed by NMR techniques (INADEQUATE). The fenchonesulfonic acid obtained is converted (SOCl2/NH3) to the cyclic fenchonesulfonimide, which can be oxidized to the corresponding oxaziridine, in close analogy to 10-camphorsulfonimide. Improved procedures for this reaction sequences are given. During the treatment of the sulfonic acid with thionyl chloride, a byproduct with a rearranged bicyclic skeleton is observed whose structure has been determined by ozonolytic degradation and NMR techniques. A possible mechanism for this rearrangement is suggested, based on MNDO calculations of the intermediate carbocations. The fenchonesulfonyloxaziridine oxidizes sulfides to chiral sulfoxides with appreciable enantiomeric excess, but very low reaction rate. A comparison with camphor-derived oxaziridines having similar steric requirements is made.

Asymmetric synthesis of both enantiomers of 2.5-hexane diol and 2.6-heptane diol induced by chiral sulfoxides

1994 ◽  
Vol 35 (29) ◽  
pp. 5297-5300 ◽  
Author(s):  
Guy Solladié ◽  
Nathalie Huser ◽  
José Luis Garcia-Ruano ◽  
Javier Adrio ◽  
M.Carmen Carreño ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Sulfoxides

scholarly journals Isolation of Rhodococcus sp. Strain ECU0066, a New Sulfide Monooxygenase-Producing Strain for Asymmetric Sulfoxidation

2008 ◽  
Vol 75 (2) ◽  
pp. 551-556 ◽  
Author(s):  
Ai-Tao Li ◽  
Jian-Dong Zhang ◽  
Jian-He Xu ◽  
Wen-Ya Lu ◽  
Guo-Qiang Lin
Keyword(s):  
Enzyme Activity ◽  
Asymmetric Synthesis ◽  
Bacterial Strain ◽  
Enantiomeric Excess ◽  
Good Activity ◽  
Rich Medium ◽  
Practical Application ◽  
Chiral Sulfoxides ◽  
Good Potential ◽  
Rhodococcus Sp

ABSTRACT A new and efficient sulfide monooxygenase-producing strain, ECU0066, was isolated and identified as a Rhodococcus sp. that could transform phenylmethyl sulfide (PMS) to (S)-sulfoxide with 99% enantiomeric excess via two steps of enantioselective oxidations. Its enzyme activity could be effectively induced by adding PMS or phenylmethyl sulfoxide (PMSO) directly to a rich medium at the early log phase (6 h) of fermentation, resulting in over 10-times-higher production of the enzyme. This bacterial strain also displayed fairly good activity and enantioselectivity toward seven other sulfides, indicating a good potential for practical application in asymmetric synthesis of chiral sulfoxides.

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