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A Gold Carbene Manifold to Prepare Fused γ‐Lactams by Oxidative Cyclisation of Ynamides
Author(s) -
SánchezCantalejo Fernando,
Priest Joshua D.,
Davies Paul W.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804378
Subject(s) - carbene , chemistry , substituent , combinatorial chemistry , catalysis , aryl , complementarity (molecular biology) , oxidative phosphorylation , organic chemistry , alkyl , biology , genetics , biochemistry
Gold‐catalysed oxidative cyclisation reactions of ynamides offer great promise in γ‐lactam synthesis but are limited by preferential over‐oxidation to form α‐keto imides. Evaluating the factors that might limit N ‐cyclisation pathways led to effective gold‐catalysed conditions that allow access to different fused γ‐lactams on changing the ynamide N ‐substituent and accommodate previously incompatible substitution patterns. New and efficient methods for the synthesis of functionalised 3‐aryl indoles and cyclohepta[c]pyrrol‐1‐one derivatives are presented. These conditions illustrate the complementarity of gold catalysis to other metals.