Abstract

Metallo-azomethine ylides, generated from iminophosphonates in combination with LiBr or AgOAc and bases Et 3N, DBU, t-butyl tetramethylguanidine(BTMG) undergo cycloaddition to give dialkyl pyrrolidine-2-phosphonates along with the corresponding Michael adduct in some cases. Cycloadditions with the chiral dipolarophile 5 R-(1′ R,2′ S,5′ R-menthyloxy)-2-(5 H)-furanone (MOF) afforded enantiopure cycloadducts.

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