112375-42-5Relevant articles and documents
Synthesis of Isomerically Pure (Z)-Alkenes from Terminal Alkynes and Terminal Alkenes: Silver-Catalyzed Hydroalkylation of Alkynes
Lee, Mitchell T.,Goodstein, Madison B.,Lalic, Gojko
, p. 17086 - 17091 (2019)
Alkenes are an important class of compounds common among biologically active molecules and often are used as intermediates in organic synthesis. Many alkenes exist in two stereoisomeric forms (E and Z), which have different structures and different properties. The selective formation of the two isomers is an important synthetic goal that has long inspired the development of new synthetic methods. However, the efficient synthesis of diastereopure, thermodynamically less stable, Z-alkenes is still challenging. Here, we demonstrate an efficient synthesis of diastereopure Z-alkenes (Z:E > 300:1) through a silver-catalyzed hydroalkylation of terminal alkynes, using alkylboranes as coupling partners. We also describe the exploration of the substrate scope, which reveals the broad functional group compatibility of the new method. Preliminary mechanistic studies suggest that a 1,2-metalate rearrangement of the silver borate intermediate is the key step responsible for the stereochemical outcome of the reaction.
The Capsaicinoids: Their Separation, Synthesis, and Mutagenicity
Gannett, Peter M.,Nagel, Donald L.,Reilly, Pam J.,Lawson, Terence,Sharpe, Jody,Toth, Bela
, p. 1064 - 1071 (2007/10/02)
Capsaicin (1b), the pungent ingredient in many varietes of Capsicums has recently been implicated as a possible carcinogen.When obtained from natural sources 1b is always accompanied by a number of related homologues.We have isolated seven of these homologues, characterized them, and synthesized them by a general and unique route developed in our laboratories.Also reported are mutagenicity data for 1b and an extract of red pepper as measured by the Ames assay and the V-79 mammalian cell assay.
