Issue 10, 2010

Construction of perhydro indol-2-ones by a methoxide catalyzed deacetylation–Michael–aldol cascade

Abstract

An efficient, stereoselective Michael–aldol cascade for the one-pot construction of the perhydro indol-2-one bicyclic ring system using an acetate protected doubly-activated pyrrole-2-one pro-nucleophile and α,β-unsaturated carbonyl compounds has been developed. Initiated by a methoxide deacetylation in methanol at room temperature, the cascade is easy to perform, stereoselective, efficient and broad in scope to this synthetically relevant structure.

Graphical abstract: Construction of perhydro indol-2-ones by a methoxide catalyzed deacetylation–Michael–aldol cascade

Supplementary files

Article information

Article type
Communication
Submitted
24 nóv. 2009
Accepted
22 des. 2009
First published
13 jan. 2010

Chem. Commun., 2010,46, 1691-1693

Construction of perhydro indol-2-ones by a methoxide catalyzed deacetylation–Michael–aldol cascade

J. W. Ward, K. Dodd, C. L. Rigby, C. De Savi and D. J. Dixon, Chem. Commun., 2010, 46, 1691 DOI: 10.1039/B924637A

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