Synthesis of quinine and quinidine using sulfur ylide-mediated asymmetric epoxidation as a key step
نویسندگان
چکیده
Article history: Received 13 April 2010 Accepted 28 April 2010 Available online 16 June 2010 Dedicated to Henri Kagan on the occasion of his 80th birthday 0957-4166/$ see front matter 2010 Elsevier Ltd. A doi:10.1016/j.tetasy.2010.04.046 * Corresponding author. Tel.: +44 117 954 6315; fa E-mail address: [email protected] (V.K. Agg The epoxidation of meroquinene aldehyde with a chiral sulfur ylide as the key step in the synthesis of quinine and quinidine is described. The epoxidation reactions proceed under reagent control with high selectivity and good yield. The effect of sulfide and ylide substituents on the stereochemical outcome of the reaction is discussed. 2010 Elsevier Ltd. All rights reserved.
منابع مشابه
Practical and highly selective sulfur ylide mediated asymmetric epoxidations and aziridinations using an inexpensive, readily available chiral sulfide. Applications to the synthesis of quinine and quinidine.
Heating one of the most abundant naturally occurring inorganic chemicals (elemental sulfur) with one of the most readily available homochiral molecules (limonene) gives a one-step synthesis of a chiral sulfide which exhibits outstanding selectivities in sulfur ylide mediated asymmetric epoxidations and aziridinations. In particular reactions of benzyl and allylic sulfonium salts with both aroma...
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