Whitby group

 

This post is compatible for submission to ChemSpider Reactions. See [blog=44639]ChemSpider Reactions template - help and further information[/blog] for help when using it. Reaction information *#Reaction file [data]37727[/data] *Reaction file type  CDX *Procedure n-BuLi (0.80 mL of a 2.5 M solution in hexanes, 2.0 mmol) was added dropwise to a solution of Cp2ZrCl2 (293 mg, 1.0 mmol) in dry THF (5.0 mL) at −78 °C.  A solution of ynamide 117a (360 mg, 1.0 mmol) in dry THF (3.0 mL) was added dropwise at −78 °C.  The reaction mixture was warmed to room temperature and stirred for 2 h.  The reaction mixture was cooled to 0 °C and iodine (508 mg, 2.0 mmol) and CuCl (99.0 mg, 1.0 mmol) added.  The reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was poured into sat. aq. ammonium chloride solution (100 mL) and extracted with ether (3 × 50 mL).  The organic extracts were combined, washed sequentially with sat. aq. Na2S2O3 solution (100 mL), and sat. aq. NaHCO3 solution (100 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product as an orange oil (758 mg). Purification by column chromatography (SiO2, hexane/Et2O 4:1) gave the title compound as an orange oil (573 mg, 91%).    *Yield (%)  91% *Type of Yield  Isolated product yield Reference(s)  [data]37103[/data][data]37101[/data] Further information  Compound 127a: (2E,3Z)-2,3-Bis(1-iodopentylidene)-1-tosylpyrrolidine For multistep reactions (or their steps): Overall reaction?  True For overall reaction - links to child reaction steps   For step in multistep reaction - link to previous reaction step   For step in multistep reaction - link to following reaction step