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2005
Rearrangements
O 0140
Ruthenium Porphyrin Catalyzed Tandem Sulfonium/Ammonium Ylide Formaand [2,3]-Sigmatropic Rearrangement. A Concise Synthesis of (±)-Platyne07- 039 tion
cine. — In the presence of ruthenium porphyrin, diazo compounds react with allyl sulfides and amines to afford ylides which rearrange to products of type (III). The reaction
proceeds with or without low stereoselectivity but high chemoselectivity. An intramolecular version is also possible giving cyclic molecules like (XI) and (XIII). This method can be applied successfully to prepare alkaloids such as platynecine (XVI). —
(ZHOU, C.-Y.; YU*, W.-Y.; CHAN, P. W. H.; CHE*, C.-M.; J. Org. Chem. 69 (2004)
21, 7072-7082; Dep. Chem., Univ. Hong Kong, Kowloon, Hong Kong, Peop. Rep.
China; Eng.) — Jannicke
2005
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