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Diastereoselective Synthesis of Cyclopentene Spiro-rhodanines Containing Three Contiguous Stereocenters via Phosphine-catalyzed [3+2] Cycloaddition or One-pot Sequential [3+2]/[3+2] Cycloaddition

Zhiwei Miao and Jiayong Zhang *

Two different diastereoselective phosphine-catalyzed cascade reactions to form cyclopentene spiro-rhodanine scaffolds are described. In the first approach, alkynoate derivatives and 5-arylidene-3-(tert-butyl)-2-thioxothiazolidin-4-one react in the presence of PBu3 through a [3+2] cycloaddition to afford 5-spiro-cyclopentene-rhodanines in high yields (up to 99%) and with excellent diastereoselectivities [20:1 diastereomeric ratio (dr)]. In the second approach, the sequential [3+2]/[3+2] annulation reaction of ethyl 5-phenylpent-2-ynoate, substituted arylethylpropiolates, amines, and carbon disulfide with phosphine catalysis produces the corresponding monospirocyclic rhodanine products in good yields (up to 92%) and with excellent diastereoselectivities (up to 20:1 dr) (Scheme 1)