Ru(salen)-catalyzed asymmetric sulfimidation and subsequent [2,3]sigmatropic rearrangement

Chirality

Volumn 15, Issue 2, 2003, Pages 116-123

  Murakami, Masakazu ^a   Uchida, Tatsuya ^a   Saito, Bunnai ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

2,3 sigmatropic rearrangement; Asymmetric catalysis; Asymmetric sulfimidation; C N bond formation; Ruthenium(salen) complex

Indexed keywords

ALLYL SULFIDE; RUTHENIUM; SULFIDE; TOLUENESULFONAMIDE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0037258155     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.10156     Document Type: Article

References (30)

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22. A part of this study has been communicated: (a) Murakami M, Uchida T, Katsuki, T. Ru (salen)-catalyzed asymmetric sulfimidation using arylsulfonyl azide. Tetrahedron Lett 2001;42:7071-7074. (b) Murakami M, Katsuki T. Chiral (OC)Ru(salen)-catalyzed tandem sulfimidation and [2,3]sigmatropic rearrangement: asymmetric C-N bond formation. Tetrahedron Lett 2002;43:3947-3949.
23. A part of this study has been communicated: (a) Murakami M, Uchida T, Katsuki, T. Ru (salen)-catalyzed asymmetric sulfimidation using arylsulfonyl azide. Tetrahedron Lett 2001;42:7071-7074. (b) Murakami M, Katsuki T. Chiral (OC)Ru(salen)-catalyzed tandem sulfimidation and [2,3]sigmatropic rearrangement: asymmetric C-N bond formation. Tetrahedron Lett 2002;43:3947-3949.
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30. A similar stereochemistry was observed in the [2,3]sigmatropic rearrangement of S-ylides derived from allyl sulfides: the reactions of E-and Z-cinnamyl phenyl sulfides gave the same product. Fukuda T, Irie R, Katsuki T. Catalytic asymmetric [2,3]sigmatropic rearrangement: Co(III)-salen catalyzed S-ylide formation from allyl aryl sulfides and their rearrangement. Tetrahedron 1999;55:649-664.