Gold‐ and Copper‐Catalyzed Cycloisomerizations towards the Synthesis of Thujopsanone‐Like Compounds

Autor:	Jeremy Arpagaus, Magali Vuagnoux, Andrea K. Buzas, Horst Sommer, Charles Fehr
Rok vydání:	2011
Předmět:	Cycloisomerization Bicyclic molecule chemistry Organic Chemistry Copper catalyzed Organic chemistry chemistry.chemical_element General Chemistry Copper Medicinal chemistry Catalysis Ether formation
Zdroj:	Chemistry – A European Journal. 17:6214-6220
ISSN:	1521-3765 0947-6539
DOI:	10.1002/chem.201002797
Popis:	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.
Databáze:	OpenAIRE
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