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22nd August 2013 @ 14:39

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*Reaction file type CDX

General procedure C with 4-Methyl-N-(4-(trimethylsilyl)but-3-yn-1-yl)-N-((trimethylsilyl)ethynyl)benzenesulfonamide (392 mg, 1.0 mmol).  Purification by column chromatography (SiO2, hexane/Et2O 4:1) gave the the major product as a pale yellow oil (147 mg, 37%). 

 The minor product (title compound) was (3E)‑2‑(tosyl(trimethylsilyl)methylene)‑3‑((trimethylsilyl)methylene)pyrrolidine, obtained as a pale yellow oil (70.6 mg, 18%)

General procedure C: zirconocene mediated cocyclisation of ynamides

n-BuLi (0.88 mL of a 2.5 M solution in hexanes, 2.2 mmol) was added dropwise to a solution of Cp2ZrCl2 (322 mg, 1.1 mmol) in dry THF (5.0 mL) at −78 °C.  A solution of the appropriate ynamide (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 5 h.  The reaction mixture was cooled to −78 °C and MeOH (10.0 mL) added.  After stirring at −78 °C for 1 h the reaction mixture was stirred at room temperature for 16 h.  The reaction mixture was poured into water (100 mL) and extracted with ether (3 × 50 mL).  The organic extracts were combined, washed sequentially with water (2 × 100 mL) and brine (100 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product, which was purified as described.


*Yield (%)  18
*Type of Yield Isolated product yield
AH Thesis_2011_pp97.pdf
AH Thesis_2011_pp176-223.pdf
Further information  Compound 126i: (3E)‑2‑(tosyl(trimethylsilyl)methylene)‑3‑((trimethylsilyl)methylene)pyrrolidine

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Attached Files
AH Thesis_2011_pp97.pdf
AH Thesis_2011_pp176-223.pdf