Geminal Bis(sulfoximine)s: Synthesis and Applications in Asymmetric Catalysis
2004; Wiley; Volume: 346; Issue: 11 Linguagem: Inglês
10.1002/adsc.200404164
ISSN1615-4169
AutoresMichael Reggelin, Heinz Weinberger, V. Spohr,
Tópico(s)Sulfur-Based Synthesis Techniques
ResumoAbstract A number of C 2 ‐symmetrical geminal bis(sulfoximine)s have been prepared for the first time and used as ligands in boron‐mediated reductions of acetophenone and copper complex‐catalyzed 1,4‐additions of diethylzinc to 2‐cyclohexenone. The copper complex of bis(sulfoximine) 46 was found to be highly active in this type of reaction, furnishing the addition product in nearly quantitative yield even at −90 °C. From the reaction of bis(sulfoximine) 42 with Cu(OTf) 2 a copper complex was isolated and characterized by X‐ray structural analysis. A mixture of SES‐Cl and NaN 3 in acetonitrile was found to behave like SES‐N 3 in FeCl 2 ‐mediated iminations of sulfoxides, affording the corresponding sulfoximines with complete retention of the sulfur configuration.
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