Highly diastereoselective additions to polyhydroxylated pyrrolidine cyclic imines: ready elaboration of aza??sugar scaffolds to create diverse carbohydrate??processing …

TM Chapman, S Courtney, P Hay…

Index: Chapman, Timothy M.; Courtney, Steve; Hay, Phil; Davis, Benjamin G. Chemistry - A European Journal, 2003 , vol. 9, # 14 p. 3397 - 3414

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Citation Number: 90

Abstract

Abstract Representative diastereomeric, erythritol and threitol polyhydroxylated pyrrolidine imine scaffolds have been rapidly elaborated to diversely functionalized aza-sugars through highly diastereoselective organometallic (RM) additions (R= Me, Et, allyl, hexenyl, Ph, Bn, pMeO-Bn). The yields for these additions have all been substantially enhanced from previously optimised levels (< 58%) for normal additions using a reverse addition ...