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Communication | Special issue | Vol 54, No. 2, 2001, pp.623-628
Published online, 1st January, 1970
DOI: 10.3987/COM-00-S(I)102
Enantiocontrol in Tandem Allylic Sulfonium Ylide Generation and [2,3] Sigmatropic Rearrangement Catalyzed by Chiral Dirhodium(II) Complexes

Shinji Kitagaki, Yoshimasa Yanamoto, Hisae Okubo, Makoto Nakajima, and Shunichi Hashimoto*

*Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan


Tandem sulfonium ylide formation and [2,3] sigmatropic rearrangement sequence from allylic sulfides and diazoacetates has been effected by using dirhodium(II) tetrakis[3(S)-phthalimido-2-piperidinonate], Rh2(S-PTPI)4, as a chiral catalyst, displaying enantioselectivities of up to 58%. It has been demonstrated that the [2,3] sigmatropic rearrangement proceeds through chiral, nonracemic free sulfonium ylides dissociated from the dirhodium(II) complex.