Application of a novel 1,3-diol with a benzyl backbone as chiral ligand for asymmetric oxidation of sulfides to sulfoxides

Gogoi, Paramartha; Kotipalli, Trimurthulu; Indukuri, Kiran; Bondalapati, Somasekhar; Saha, Pipas; Saikia, Anil K.

doi:10.1016/j.tetlet.2012.03.077

Cited by 16 publications

(11 citation statements)

References 58 publications

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“…s, 1 H, 1-H). The preceding data are consistent with those reported in the literature 53. The ee was determined by chiral HPLC (Chiralcel OD-3, n-heptane/i-PrOH 98:2, 1 mL/min, λ detector = 224 nm): t r (R) =13.40 min, t r (S) = 15.81 min.…”

supporting

confidence: 89%

“…45 The racemic synthesis 44 The preceding data are consistent with those reported in the literature. 53 The ee was determined by chiral HPLC (Chiralcel OJ-H, n-heptane/ EtOH 95:5, 1 mL/min, λ detector = 250 nm): t r (R) = 51 Butyl Phenyl Sulfoxide (36): (S)-(−)-Enantiomer and Racemic. 45 The racemic synthesis 44 The absolute configuration was determined by comparing the sense of the optical rotation with literature data.…”

Section: ■ Conclusionmentioning

confidence: 99%

“…45 The racemic synthesis 44 The absolute configuration was determined by comparing the sense of the optical rotation with literature data. 53 Butyl (p-Tolyl) Sulfoxide ( 37): (S)-(−)-Enantiomer and Racemic. 45 The racemic synthesis 44 2 in acetone, a sample of the (S)-enantiomer with 91% ee).…”

Section: ■ Conclusionmentioning

confidence: 99%

“…45 The racemic synthesis 44 Butyl (2-Naphthyl) Sulfoxide ( 42): (S)-(−)-Enantiomer and Racemic. 45 The racemic synthesis 44 53 Isobutyl Phenyl Sulfoxide ( 43): (S)-(−)-Enantiomer and Racemic. 45 The racemic synthesis 44 50 Isobutyl (2,4,6-Trimethylphenyl) Sulfoxide ( 45): (−)-Enantiomer and Racemic.…”

Section: ■ Conclusionmentioning

confidence: 99%

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Symmetric Diarylsulfoxides as Asymmetric Sulfinylating Reagents for Dialkylmagnesium Compounds

Ruppenthal

Brückner

2014

J. Org. Chem.

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At −78 °C, primary dialkylmagnesium compounds reacted with diarylsulfoxides when 1.5 equiv of the dilithium salt of (S)-BINOL was added as a promotor. Alkyl aryl sulfoxides resulted in up to quantitative yield and with up to 97% ee. This demonstrates the feasibility of asymmetric sulfinylations by achiral sulfinylating agents (from the perspective of Alkyl2Mg) as well as the feasibility of asymmetric sulfoxide–magnesium exchanges (from the perspective of Ar2SO).

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supporting

confidence: 89%

Section: ■ Conclusionmentioning

confidence: 99%

Section: ■ Conclusionmentioning

confidence: 99%

Section: ■ Conclusionmentioning

confidence: 99%

See 2 more Smart Citations

Symmetric Diarylsulfoxides as Asymmetric Sulfinylating Reagents for Dialkylmagnesium Compounds

Ruppenthal

Brückner

2014

J. Org. Chem.

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“…A substantial stereo-induction was observed during the NaBH 4 reduction of keto functionality of 3c , an excellent diastereoselectivity (10 : 1) was achieved in the compound 9 . Further, oxidative deborylation of the product 9 produced chiral 1,3-diol 24 10 with high enantioselectivity and good diastereoselectivity. Finally, chiral benzylic alcohol 4c was treated with aldehydes in the presence of acids which furnished the acetals ( 11 and 12 ) with excellent diastereoselectivity (43 : 1 and 10 : 1, respectively), albeit a small reduction of enantioselectivity.…”

Section: Resultsmentioning

confidence: 99%