期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 17, 期 22, 页码 6214-6220出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201002797
关键词
copper; cycloisomerization; fragrances; gold; rearrangement
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 10 a 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 AuCl3) or an unprecedented rearrangement-cycloaddition leading to 20 (43% using [(tBuXPhos)AuNTf2]), a strained fused tricyclic ring system containing a [2.2.0] bicyclic subunit.
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