50281-16-8Relevant academic research and scientific papers
Development of the first menthane-based chiral bis(π-allylpalladium) catalysis: Asymmetric allylation of imines
Fernandes, Rodney A.,Chaudhari, Dipali A.
experimental part, p. 1945 - 1952 (2012/05/20)
A new ethylidene menthane-based chiral π-allylpalladium complex catalyzes the asymmetric allylation of various imines with allyltributylstannane and 1 equiv. of water to give chiral homoallylamines in good yields and enantioselectivities. The reaction was carried out essentially under neutral conditions and displayed a good transfer of chiral information from the menthane skeleton through the formation of a bis(π-allylpalladium) species. This is the first example of menthane-based chiral bis(π-allylpalladium) catalysis. A menthane-based chiral π-allylpalladium-catalyzed asymmetric allylation of various imines has been developed giving chiral homoallylamines in good yields and enantioselectivities. The reaction displays a good transfer of chiral information from the menthane skeleton through the formation of a bis(π-allylpalladium) complex. Copyright
Synthetic Routes to some Isotopically Labelled Intermediates for Diterpenoid Biosynthesis
Dawson, Raymond M.,Godfrey, Ian M.,Hogg, Ronald W.,Knox, John R.
, p. 561 - 580 (2007/10/02)
The exo-15-hydrogen of ent-kauren can be exchanged through a reversible ene reaction in a convention and efficient procedure which has the potential for giving high specific activity (3)H-labeling.Copalol, the (Z)-double bond stereoisomer, and the allylic alcohol isomers ent-manool and ent-epimanool have been obtained through divergent synthetic pathways involving a 15,16-bisnor ketone intermediate.These pathways have also allowed the four compounds to be obtained with (14)C-labelling.A method, involving a Wittig reaction to form a vinyl bromide intermediate, has been developed for obtaining copalol, as the trityl ether derivative, with stereospecific isotopic labelling of one or the other of the hydrogens of the exocyclic methylene group.
