Catalytic asymmetric sulfimidation
UNSPECIFIED. (1997) Catalytic asymmetric sulfimidation. JOURNAL OF ORGANIC CHEMISTRY, 62 (19). pp. 6512-6518. ISSN 0022-3263Full text not available from this repository.
A direct catalytic imidation of sulfides to sulfimides with [N-(p-tolylsulfonyl)imino]phenyliodinane (TsN=IPh) using a catalytic amount of copper triflate (CuOTf) has been developed. The reaction proceeds with a wide range of sulfides to give the corresponding sulfimides in 50-83% isolated yields. When the reaction is applied to allylic sulfides, the products are the corresponding sulfonamides produced via [2,3] sigmatropic rearrangement of the initially formed allylic sulfimides. In the presence of a chiral bis(oxazoline) as ligand, asymmetric induction occurs to afford the chiral sulfimides (up to 71% ee) and sulfonamides (up to 58% ee). Chloramine T (TsNClNa) can be used in place of TsN=IPh for asymmetric sulfimidation, but the ee's are much lower. Some mechanistic observations are described.
|Item Type:||Journal Article|
|Subjects:||Q Science > QD Chemistry|
|Journal or Publication Title:||JOURNAL OF ORGANIC CHEMISTRY|
|Publisher:||AMER CHEMICAL SOC|
|Official Date:||19 September 1997|
|Number of Pages:||7|
|Page Range:||pp. 6512-6518|
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