Gosteli-claisen rearrangement of propargyl vinyl ethers: Cascading rearrangements molecular

Organic Letters

Volumn 13, Issue 8, 2011, Pages 2122-2125

  Gille, Annika ^a   Rehbein, Julia ^a   Hiersemann, Martin ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79955423126     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200558j     Document Type: Article

References (42)

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25. 1a-g were synthesized following our aldol condensation approach; see: Hiersemann, M. Synthesis 2000, 1279-1290. For experimental procedures and characterization, see the Supporting Information.
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35. l2 at ambient temperature provided (±)-2a. We assume a rapid racemization of 2a via the enol 7a in the presence of the Lewis acid.
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40. The formation of allenes at ambient temperature under the reaction conditions indicates that the Gosteli-Claisen rearrangement proceeds under specific-acid catalysis by the hydronium ion.
41. 1a-g were also treated with PTSAH2O(0.1 equiv) in HFIP (370 ppm H2O) at ambient temperature for 23 h. In the event, furan formation was much slower for 1a-e; neither 1f nor 1g was converted into the corresponding furan. Interestingly, however, subjecting the allenes 2a and 2c to the identical conditions led to the high-yielding formation of 12a (99%) and 12c (83%).
42. We did not attempt a rigorous optimization of the catalyst loading.