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A Gold Carbene Manifold to Prepare Fused ?-Lactams by Oxidative Cyclisation of Ynamides.


ABSTRACT: Gold-catalysed oxidative cyclisation reactions of ynamides offer great promise in ?-lactam synthesis but are limited by preferential over-oxidation to form ?-keto imides. Evaluating the factors that might limit N-cyclisation pathways led to effective gold-catalysed conditions that allow access to different fused ?-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.

SUBMITTER: Sanchez-Cantalejo F 

PROVIDER: S-EPMC6282577 | BioStudies | 2018-01-01T00:00:00Z

REPOSITORIES: biostudies

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