AI Article Synopsis
- Researchers explored new methods to create thujopsanone compounds through cycloisomerization of unsaturated propargylic alcohols and acetates.
- They identified effective catalysts, mainly gold (Au), platinum (Pt), and copper (Cu), with Au and a new Cu catalyst yielding high reaction rates (up to 98%).
- Noteworthy reactions included a clean cyclization/ether formation process and an unusual rearrangement-cycloaddition resulting in a complicated tricyclic structure.
Article Abstract
In the search for a new access to thujopsanone related compounds by cycloisomerization reactions of unsaturated propargylic alcohols and acetates, we found several interesting reaction types and demonstrated the complementarity of Au, Pt, and Cu catalysts. Thus, 6-en-1-yn-3-ol 10a underwent clean cyclization/ether formation to 16, in particular using Au catalysts (76-98%) or a newly prepared Cu(I)-triflimidate-catalyst (94%). The corresponding acetate 11 a underwent either the cycloisomerization with concomitant [1,2]-acyl shift (to 12: 78% using AuCl(3)) or an unprecedented rearrangement-cycloaddition leading to 20 (43% using [(tBuXPhos)AuNTf(2)]), a strained fused tricyclic ring system containing a [2.2.0] bicyclic subunit.
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| http://dx.doi.org/10.1002/chem.201002797 | DOI Listing |
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