title: Enantioselective catalytic desymmetrization of maleimides by temporary removal of an internal mirror plane and stereoablative over-reduction: synthesis of (R)-pyrrolam A.
abstract: A highly enantioselective (>95% ee) strategy to affect the desymmetrization of a maleimide has been performed by temporary attachment to an anthracene template followed by asymmetric reduction with an oxazaborolidine catalyst. A stereoablative over-reduction process was partially responsible for the high levels of enantioselectivity. Exemplification of the strategy by stereoselective functionalization and retro-Diels-Alder reaction provided the natural product pyrrolam A.
authors: Department of Chemistry, University of Sheffield , Dainton Building, Brook Hill, Sheffield S3 7HF, United Kingdom.
authors: Barrie J
authors: BJ
authors: Marsh
authors: Harry
authors: H
authors: Adams
authors: Mike D
authors: MD
authors: Barker
authors: Ibrahim U
authors: IU
authors: Kutama
authors: Simon
authors: S
authors: Jones
mesh_terms: D000873:Anthracenes / Q000737:chemistry; D002384:Catalysis; D061565:Cycloaddition Reaction; D008301:Maleimides / Q000737:chemistry*; D015394:Molecular Structure; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000873:Anthracenes; D008301:Maleimides; D011763:Pyrrolizidine Alkaloids; C419422:pyrrolam A; C043592:maleimide; C034020:anthracene