157427-19-5Relevant articles and documents
Gold-catalyzed synthesis of oxygen- and nitrogen-containing heterocycles from alkynyl ethers: Application to the total synthesis of andrachcinidine
Hyung, Hoon Jung,Floreancig, Paul E.
, p. 7359 - 7366 (2008/02/11)
(Chemical Equation Presented) In this paper we report that homopropargylic ethers containing pendent oxygen or nitrogen nucleophiles react with electrophilic gold catalysts in the presence of water to form saturated heterocyclic ketones. Mechanistic studies demonstrated that the reactions proceed through a sequence of alkyne hydration, alkoxy group elimination, and intramolecular conjugate addition. Diastereoselectivities for tetrahydropyran and piperidine formation are very good to excellent. This method has been applied to an efficient total synthesis of the natural product andrachcinidine. Utilizing propargylic ether substrates rather than homopropargylic ethers promotes regioselective hydration of internal alkynes, thereby expanding the scope of products that can be accessed through this protocol.
Gold-catalyzed heterocycle synthesis using homopropargylic ethers as latent electrophiles
Jung, Hyung Hoon,Floreancig, Paul E.
, p. 1949 - 1951 (2007/10/03)
Homopropargylic ethers with pendent nucleophiles, when subjected to Au catalysts in aqueous solvent, provide heterocyclic ketones. The reactions are efficient, tolerant of functionality and ambient atmosphere, and operationally simple. Diastereoselectivity can be predicted on the basis of product thermodynamics. This process demonstrates the viability of homopropargylic ethers to serve as latent electrophiles that can be unraveled under highly selective conditions to promote heterocycle formation through nucleophilic additions to α,β-unsaturated ketones.
Aldol Reaction of Enol Acetates and Lactols with N-Chlorosuccinimide and Tin(II) Chloride. Diastereoselective Synthesis of Disubstituted Cyclic Ethers
Masuyama, Yoshiro,Kobayashi, Yumiko,Kurusu, Yasuhiko
, p. 1123 - 1124 (2007/10/02)
Lactols reacted with enol acetates by a Lewis acid reagent, derived from N-chlorosuccinimide and tin(II) chloride, to produce 2-acetonyl cyclic ethers diastereoselectively.
