S-Oxidation products of (+)-thiomicamine-derived oxazolines—promising substrates in the synthesis of alkyl methyl sulfoxides

Brózda, Danuta; Głuszyńska, Agata; Kościołowicz, Agnieszka; Rozwadowska, Maria D.

doi:10.1016/j.tetasy.2005.01.027

Cited by 3 publications

(5 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…These chiral tert -butyl sulfinates were converted into chiral sulfoxides with high yields and >96% ee . Sulfoxide 134 bearing the oxazoline ring was used as the chiral methylsulfinyl group transfer agent . Its reaction with butyllithium reagents proceeded with moderate (47−52%) yield, but high enantiomeric purity was preserved (92−99% ee ).…”

Section: Chemical Methods Of Nonracemic Sulfoxide Preparationmentioning

confidence: 99%

“…Among these Schiff bases, the best yield (97%) and enantiomeric excess (43%, increased by recrystallization to >99%) were observed for compound 209 , bearing only one stereogenic center. Other Schiff bases (two of them, 210 and 211 , prepared for the first time) were used by this group for the oxidation of oxazoline-derived sulfides 103 . The de values ranged from 0 to 99%, with diiodo-substituted leucinol derivative 192 being most efficient.…”

Section: Chemical Methods Of Nonracemic Sulfoxide Preparationmentioning

confidence: 99%

“…Two stereogenic centers present in oxazoline derivatives 103 were found to be insufficient for the effective 1,8asymmetric induction in the synthesis of the corresponding sulfoxides using achiral oxidants (NaOCl/TEMPO, Br 2 /H 2 O/ NaHCO 3 , mCPBA). 165 These potential chiral methylsulfinyl group transfer reagents were thus obtained using the Kagan methodology in 66-98% yield and with de's exceeding 95%. The (R) absolute configuration was assigned to the newly created chiral center.…”

Section: Oxidation Using Metal Complexesmentioning

confidence: 99%

“…Sulfoxide 134 bearing the oxazoline ring was used as the chiral methylsulfinyl group transfer agent. 165 Its reaction with butyllithium reagents proceeded with moderate (47-52%) yield, but high enantiomeric purity was preserved (92-99% ee).…”

Section: C-s Bond Formationmentioning

confidence: 99%

“…Other Schiff bases (two of them, 210 and 211, prepared for the first time) were used by this group for the oxidation of oxazoline-derived sulfides 103. 165 The de values ranged from 0 to 99%, with diiodo-substituted leucinol derivative 192 being most efficient.…”

Section: Oxidations Catalyzed By Metal Complexesmentioning

confidence: 99%

See 4 more Smart Citations

Enantioselective Synthesis of Sulfoxides: 2000−2009

2010

View full text Add to dashboard Cite

Elz ˙bieta Wojaczyn ´ska (ne ´e Ostrycharz) was born in Z ˙migród, Poland. She received her M.Sc. degree in organic chemistry from Wrocław University of Technology in 1997. Her doctoral thesis on the enantioselective synthesis and application of chiral sulfoxides was completed under the supervision of Professor Jacek Skarz ˙ewski in 2001. Her research at the Department of Organic Chemistry of the Wrocław University of Technology focuses on the synthesis of new chiral building blocks and of novel chiral ligands for the asymmetric synthesis. Jacek Wojaczyn ´ski was born in Wrocław in 1969. He graduated from the University of Wrocław in inorganic chemistry in 1993. He received his Ph.D. in 1998 for work on the influence of asymmetric modification of the porphyrin periphery on the properties of formed complexes. He is a member of the Porphyrin Chemistry Research Group led by Professor Lechosław Latos-Graz ˙yn ´ski at the Department of Chemistry, University of Wrocław. His current scientific interests include degradation of tetrapyrrolic macrocycles and investigation of paramagnetic hemoproteins using NMR spectroscopy.

show abstract

Section: Chemical Methods Of Nonracemic Sulfoxide Preparationmentioning

confidence: 99%

Section: Chemical Methods Of Nonracemic Sulfoxide Preparationmentioning

confidence: 99%

Section: Oxidation Using Metal Complexesmentioning

confidence: 99%

Section: C-s Bond Formationmentioning

confidence: 99%

Section: Oxidations Catalyzed By Metal Complexesmentioning

confidence: 99%

See 3 more Smart Citations

Enantioselective Synthesis of Sulfoxides: 2000−2009

2010

View full text Add to dashboard Cite

show abstract

Oxoammonium‐ and Nitroxide‐Catalyzed Oxidations of Alcohols

2009

View full text Add to dashboard Cite

The discovery in 1959 of stable nitroxide‐based free radicals such as the prototypical 2,2,6,6‐tetramethylpiperidine‐1‐oxyl (TEMPO) led to their use as electron spin resonance (ESR) spin labels in chemistry, biomedicine, and materials science. These nitroxides are prepared by the oxidation of secondary amines that contain no hydrogen atoms on the alpha‐carbons. The unique redox properties of nitroxides enable their use as oxidants in organic synthesis. The varied preparation and uses of oxoammonium salts as stoichiometric oxidants for alcohols are one subject of this review. Oxoammonium ions as oxidants for alcohols have a number of advantages, for example, the method is heavy‐metal free and some of the reactions can be performed in water or aqueous mixtures. A few side reactions are associated with these oxidations. The most serious is the fast reaction of the oxoammonium ion with free amines The several ways these oxidation reactions can be carried out are discussed in detail. They are: Oxidations using stoichimetric quantities of preformed oxoammonium salts carried out in either acidic, neutral, or basic conditions; reactions in which stoichiometric quantities of oxoammonium salts are generated in situ by disproportionation of a nitroxide in the presence of a strong acid; nitroxide‐catalyzed oxidations using a secondary oxidant; efficient nitroxide‐catalyzed oxidations of primary alcohols to carboxylic acids; and oxidations of primary alcohols or hemiacetals that can lead to lactones.

show abstract