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New chiral thiosquaramides and their applications in catalytic asymmetric double addition of 5-methyl-2(3H)-furanones to nitroolefins were described. Enantiomerically enriched 2,4,4-trisubstituted butenolides bearing a quaternary stereogenic center could be smoothly constructed with high diastereoselectivities (up to >99 : 1 dr) and excellent enantioselectivities (up to 95% ee) under mild conditions.

Graphical abstract: Thiosquaramide-catalysed asymmetric double Michael addition of 2-(3H)-furanones to nitroolefines

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