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Making two C-C bonds and four stereocenters in one fell swoop A new catalytic domino reaction combines two acyclic starting materials to yield optically active cyclohexanones with up to four stereogenic centers [Angew. Chem. Int. Ed., published online Feb. 11, http://www3.interscience.wiley.com/cgi-bin/abstract/107614801]. Domino reactions permit multiple reaction steps to be accomplished in one reaction "pot." Karl A. Jørgensen's group at Aarhus University, in Denmark, devised a domino reaction in which a known phenylalanine-derived imidazolidine catalyst is used to accelerate both a Michael reaction (which adds an acyclic -ketoester to an acyclic unsaturated ketone) and a subsequent aldol reaction (which cyclizes the intermediate made in the first step). "I find it stunning that in one very simple reaction, Jørgensen and coworkers are able to form two C-C bonds and set the configuration of four stereocenters in a highly enantio- and diastereoselective process," comments Carlos F. Barbas III of Scripps Research Institute |
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