724762-24-7Relevant academic research and scientific papers
Supramolecular photochirogenesis with carbenes entrapped in cyclodextrins
Mieusset, Jean-Luc,Wagner, Gerald,Su, Kuan-Jen,Steurer, Marianne,Pacar, Mirjana,Abraham, Michael,Brinker, Udo H.
, p. 5907 - 5912 (2009)
Two achiral diazirines 1a and 1b have been encapsulated in the inherently chiral cavity of α-cyclodextrin (6-Cy), β-cyclodextrin (7-Cy) and permethylated β-cyclodextrin (TRIMEB) and photolyzed. Because of supramolecular photochirogenesis the generated carbenes afford intramolecular C-H insertion products not as a racemate but one enantiomer is slightly favored. With 1a at the (6-Cy)2 the ee of product 7a is doubled. To the best of our knowledge for the first time for carbene -reactions, products are imprinted, though modestly, with handedness derived from Cys. The reaction of lb is highly dependent on the molecular reactor used for inclusion. Whereas 7-Cy is very efficient for favoring dimerization through azine formation, the use of TRIMEB permits exclusive formation of intramolecular insertion product 7b.
