1301262-75-8Relevant academic research and scientific papers
A mild and efficient CH2-extrusion reaction for the enantiospecific synthesis of highly configurationally stable tr?ger bases
Pujari, Sandip A.,Besnard, Céline,Bürgi, Thomas,Lacour, Jér?me
supporting information, p. 7520 - 7523 (2015/06/25)
A novel CH2-extrusion reaction leading to the transformation of ethano-Tr?ger bases into disubstituted methano derivatives is reported (yields up to 93%). Under mild and metal-free oxidative conditions, a loss of CH2 and a ring contraction are provoked. Despite two bond cleavages at stereogenic nitrogen and carbon centers and a temporary rupture of the bicyclic structure, a very high enantiospecificity (es≥98%) is observed for this unusual reaction. Against all odds: Simple treatment of ethano-Tr?ger bases with DDQ in wet nitromethane provokes a novel CH2-extrusion reaction. Disubstituted methano-derivatives are formed in high yield and enantiospecificity despite undergoing two bond cleavages at stereogenic nitrogen and carbon centers, and a temporary rupture of the bicyclic structure. DDQ=2,3-dichloro-5,6-dicyano-1,4-benzoquinone.
One-step catalytic asymmetric synthesis of configurationally stable troeger bases
Sharma, Ankit,Guenee, Laure,Naubron, Jean-Valere,Lacour, Jerome
supporting information; experimental part, p. 3677 - 3680 (2011/06/22)
(Chemical Equation Presented) Bridging the gap: Configurationally stable ethano-bridged Troeger bases have been prepared in a single step by the direct rhodium(II)-catalyzed reaction of methano-bridged Troeger bases and diazo esters (see scheme). The proc
