Studies on the diastereoselective reductive alkylation of (R)-phenylglycinol derived phthalimide: observation of stereoelectronic effects

Abstract

Full details of a flexible approach to N-protected (R)-3-alkyl-isoindolin-1-ones 13 via diastereoselective reductive-alkylation are described, with emphasis on the stereochemical outcome of the key diastereoselective reactions. Additional experiments allowed finding remarkable stereoelectronic effects on the reductive ring-opening reactions. (C) 2004 Elsevier Ltd. All rights reserved.