Catalytic Enantiospecific [3+2] Annulation of Aminocyclopropanes with Ketones

Benfatti, Fidesde Nanteuil, FlorianWaser, Jerome2012-05-042012-05-042012-05-04201210.1002/chem.201103971https://infoscience.epfl.ch/handle/20.500.14299/80019WOS:000302354500008The first enantiospecific [3+2] annulation of D-A amino-cyclopropanes with ketones is reported herein (see scheme; Phth = phthaloyl). The reaction is catalyzed by 5 mol % of tin(IV) chloride at -78 °C and gives aminotetra-hydrofurans bearing a C5-quaternary stereocenter in high yield, diastereoselectivity and enantio-specificity.annulationaminotetrahydrofurancatalysisD-A aminocyclopropaneenantiospecificityketonesDonor-Acceptor CyclopropanesRing-Expansion ReactionCarbonyl-CompoundsSubstituted Cyclopropanes22-Dialkoxycyclopropanecarboxylic EstersOrganic-SynthesisStereoselective-SynthesisCatalytic Enantiospecific [3+2] Annulation of Aminocyclopropanes with Ketonestext::journal::journal article::research article