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Catalytic Asymmetric Sulfimidation
作者:Hiroya Takada、Yoshiaki Nishibayashi、Kouichi Ohe、Sakae Uemura、Charlotte P. Baird、Tim J. Sparey、Paul C. Taylor
DOI:10.1021/jo970798d
日期:1997.9.1
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.
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Fedorov, N. V.; Anisimov, A. V.; Viktorova, E. A., Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, # 3, p. 507 - 511
作者:Fedorov, N. V.、Anisimov, A. V.、Viktorova, E. A.
DOI:——
日期:——
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AUXARIEVA R. G.; DANILOVA T. A.; ANISIMOV A. V.; VIKTOROVA E. A., XIMIYA GETEROTSIKL. SOEDIN., 1981, HO 5, 611-614
作者:AUXARIEVA R. G.、 DANILOVA T. A.、 ANISIMOV A. V.、 VIKTOROVA E. A.
DOI:——
日期:——
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ANISIMOV, A. V.;AUXARIEVA, R. G.;FEDOROV, N. V.;VIKTOROVA, E. A., BECTH. MGU. XIMIYA, 1983, 24, N 6, 584-588
作者:ANISIMOV, A. V.、AUXARIEVA, R. G.、FEDOROV, N. V.、VIKTOROVA, E. A.
DOI:——
日期:——
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AL-SHURA, A. M.;ANISIMOV, A. V.;VIKTOROVA, E. A., ZH. ORGAN. XIMII, 24,(1988) N 2, 443-446
作者:AL-SHURA, A. M.、ANISIMOV, A. V.、VIKTOROVA, E. A.
DOI:——
日期:——