226921-23-9Relevant academic research and scientific papers
Highly selective copper-catalyzed ring expansion of vinyl thiiranes: Application to synthesis of biotin and the heterocyclic core of plavix
Rogers, Erik,Araki, Hiroshi,Batory, Lindsay A.,McInnis, Christine E.,Njardarson, Jon T.
, p. 2768 - 2769 (2007/10/03)
We report herein a new, highly selective, mild copper-catalyzed vinyl thiirane ring-expansion protocol for the formation of 2,5-dihydrothiophenes. Preliminary substrate scope and applications of this new synthetic disconnection to the formal racemic total synthesis of biotin and the synthesis of the antiplatelet blockbuster pharmaceutical agent Plavix are described. Copyright
A general one-pot synthesis of vinyl-thiiranes and conjugated dienes
Maciagiewicz,Dybowski,Skowronska
, p. 515 - 523 (2007/10/03)
The first general synthesis of vinyl-thiiranes 7 and an effiecient preparation of conjugated dienes 8 and 9 is presented. Methodology described for the preparation of these compounds is based on the corresponding readily available thiophosphates 1 and selenophosphates 2.
New mechanistic aspects on the catalytic transformation of vinylthiiranes to mono and disubstituted 3,6-dihydro-1,2-dithiins by tungsten pentacarbonyl monoacetonitrile
Lupton, David W,Taylor, Dennis K
, p. 4517 - 4527 (2007/10/03)
Various alkyl and aryl mono- and disubstituted 3,6-dihydro-1,2-dithiins have been synthesised from their corresponding vinylthiiranes exploiting Adams' tungsten pentacarbonyl monoacetonitrile catalytic transformation. New conclusions pertaining to the rate determining step, the sensitivity of the process to precursor sterics and electronics, and the nature of various reaction intermediates are highlighted.
A general one-pot synthesis of vinyl-thiiranes and conjugated dienes
Maciagiewicz,Dybowski,Skowronska
, p. 3791 - 3794 (2007/10/03)
The first general synthesis of vinyl-thiiranes 5 and an efficient preparation of conjugated dienes 6 and 7 based on thio, and selenophosphates is described.
