1007-01-8Relevant articles and documents
Efficient electrochemical deprotection of carboxylic and amino acids from their 2-(hydroxymethyl)-1,3-dithiane (dim) esters
Barnhurst, Loren A.,Wan, Yongqin,Kutateladze, Andrei G.
, p. 799 - 801 (2000)
formula presented Carboxylic acids and amino acids are electrochemically deprotected from their 2-(hydroxymethyl)-1,3-dithiane (Dim) esters.
Addition of carboxyalkyl radicals to alkenes through a catalytic process, using a Mn(II)/Co(II)/O2 redox system
Hirase, Koji,Sakaguchi, Satoshi,Ishii, Yasutaka
, p. 5974 - 5976 (2007/10/03)
A novel strategy for production of mono- and dicarboxylic acids by the addition of carboxyalkyl radicals to alkenes and dienes, respectively, was successfully developed through a catalytic process with use of Mn(II)/Co(II)/O2 system. Thus, a variety of carboxylic acids were prepared by the reaction of alkenes and dienes with acid anhydrides in the presence of a very small amount of Mn(OAc)2 (0.5 mol %) and Co(OAc)2 (0.1 mol %) under dilute dioxygen.
Highly stereoselective tandem cyclizations of 5-hexenyllithiums: Preparation of endo-2-substituted bicyclo[2.2.1]heptanes and 3-substituted trans-bicyclo[ 3.3.0] octanes
Bailey, William F.,Khanolkar, Atmaram D.,Gavaskar, Kaustubh V.
, p. 8053 - 8060 (2007/10/02)
Tandem cyclization of diolefinic alkyllithiums, derived from acyclic diolefinic alkyl iodides by low-temperature lithium-iodine exchange, proceeds via two highly stereoselective and totally regiospecific 5-exo-trig ring closures to deliver bicyclic alkyllithiums. Trapping of the organolithium product by addition of an electrophile cleanly affords functionalized bicyclic molecules in good yield. In this way both endo-2-substituted bicyclo[2.2.1]heptanes and 3-substituted trans-bicyclo[3.3.0]octanes have been prepared in isolated yields of 65-80% from the readily available 3-(2-iodoethyl)-1,5-hexadiene (5) and 7-iodo-4-ethenyl-1-heptene (9), respectively. Attempts to effect tandem cyclization of 5,10-undecadienyllithium (11), which would be mediated by a secondary alkyllithium species, were unsuccessful. The results suggest that tandem anionic cyclization provides a convenient route to a variety of bicyclic systems not readily available by other approaches.
