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- W2969897508 abstract "Azlactones, a potent building block for the synthesis of complex molecules, have been explored in an organocatalytic Mannich reaction with protected imines. In this study, azlactones containing a propargyl substituent were employed for the first time in organocatalysis so far. The catalytically active species responsible for high enantioselectivity with substrate containing such a small linear substituent is assembled in situ from a bifunctional thiourea, prone to dimerization, and an organic acid, as evidenced by DOSY NMR. The resulting α,β‐diamino acid derivatives were subjected to further derivatization: as an example, gold‐catalyzed intramolecular hydroamination of alkynes gave chiral spirocyclic dihydropyrrole. Alternatively, related squaramide catalyst enabled a Mannich reaction of azlactones with N‐aryl or alkyl glyoxylate imines. Reduction of these adducts gave access to 2,3‐diaminobutyrolactones or 2,3‐diamino‐1,4‐diol with a tertiary and a quaternary stereocenter." @default.
- W2969897508 created "2019-08-29" @default.
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- W2969897508 date "2019-09-09" @default.
- W2969897508 modified "2023-09-30" @default.
- W2969897508 title "Transformation of Racemic Azlactones into Enantioenriched Dihydropyrroles and Lactones Enabled by Hydrogen-Bond Organocatalysis" @default.
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- W2969897508 doi "https://doi.org/10.1002/ejoc.201901052" @default.
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