Construction of perhydro indol-2-ones by a methoxide catalyzed deacetylation-Michael-aldol cascade.
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 alpha,beta-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.
Ward
John W
JW
School of Chemistry, The University of Manchester, Oxford Road, Manchester, UKM13 9PL.
Dodd
Karen
K
Rigby
Caroline L
CL
De Savi
Chris
C
Dixon
Darren J
DJ
D000107:Acetylation; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D007536:Isomerism; D000432:Methanol / Q000737:chemistry*
D000447:Aldehydes; D007211:Indoles; C116609:3-hydroxybutanal; D000432:Methanol