Gold(I)-catalysed synthesis of cyclic sulfamidates: current scope, stereochemistry and competing ene-allene cycloisomerisation

Autor:	Andreas Troester, Lorna Kennedy, Mari C. M. Higginbotham, Anita G. Lindsay, Magnus W. P. Bebbington
Rok vydání:	2015
Předmět:	chemistry.chemical_compound Chemistry Stereochemistry Allene Organic Chemistry Drug Discovery Sulfamidates Gold catalysis Hydroamination Allenes Biochemistry Ene reaction
Zdroj:	Tetrahedron. 71(4):727-737
ISSN:	0040-4020
DOI:	10.1016/j.tet.2014.11.058
Popis:	Six-membered cyclic sulfamidates are prepared in high yields by treatment of allenic sulfamates with readily available Ph3PAuNTf2. The reaction enables formation of N-substituted quaternary centres in high yields. The relative stereochemistry has been unambiguously determined. A π-rearrangement is faster than hydroamination in the case of an allyl-substituted sulfamate and a mechanism is proposed for this process.
Databáze:	OpenAIRE
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