Substrate-controlled selectivity switch in a three-component reaction: sequential synthesis of spiro-oxazolidinedione-cyclopentenones and hydroxy enaminobarbiturates in water

The additive-free [3 + 2] annulation from isatins, amino acids with 2-styrylbenzoxazoles, was described, providing a series of functional and structurally complex 3,3′-pyrrolidinyl-spirooxindole derivatives containing four contiguous and two quaternary stereogenic centers in high yields (up to 95%) and excellent diastereoselectivities (up to >25:1 dr). Interestingly, the reaction exhibits switchable regioselectivity depending on the substrate of amino acids. With proline or thioproline as the substrate, the reaction afforded α-regioselective spirooxindole skeletons. In contrast, when piperidine acid is the substrate, the reaction provided γ-regioselective spirooxindole skeletons.

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Substrate-controlled selectivity switch in a three-component reaction: sequential synthesis of spiro-oxazolidinedione-cyclopentenones and hydroxy enaminobarbiturates in water

Abstract: Spiro-oxazolidinedione-cyclopentenones and hydroxy enaminobarbiturates could be selectively formed from amines, β-dicarbonyl compounds and alloxan derivatives under catalyst-free conditions in water.

Cited by 2 publications

References 63 publications

Regioselective synthesis of functionalized cyclopent-2-enone-derived carbonylureas and enaminohydroxybarbiturates from alloxans in water

Regioselective synthesis of functionalized cyclopent-2-enone-derived carbonylureas and enaminohydroxybarbiturates from alloxans in water

Substrate-Controlled Regioselectivity Switchable [3 + 2] Annulations To Access Spirooxindole Skeletons

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