Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 88, Issue 12, Pages 7888-7892Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c02491
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A one-pot multicomponent reaction, involving Knoevenagel reaction, asymmetric epoxidation, and domino ring-opening cyclization, has been developed for the synthesis of 3-aryl/alkyl piperazin-2-ones and morpholin-2-ones. The reaction proceeds in good yields (38-90%) and high enantioselectivity (up to 99% ee), with two out of three steps being catalyzed by a quinine derived urea. The method has also been applied to the enantioselective synthesis of a key intermediate for the antiemetic drug Aprepitant.
A one-pot Knoevenagel reaction/asymmetric epoxidation/domino ring-opening cyclization (DROC) has been developed from commercial aldehydes, (phenylsulfonyl)acetonitrile, cumyl hydroperoxide, 1,2-ethylendiamines, and 1,2 ethanol amines to provide 3-aryl/alkyl piperazin-2-ones and morpholin-2-ones in yields of 38 to 90% and up to 99% ee. Two out of the three steps are stereoselectively catalyzed by a quinine derived urea. The sequence has been applied for a short enantioselective entry to a key intermediate, in both absolute configurations, involved in the synthesis of the potent antiemetic drug Aprepitant.
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