title: Highly diastereoselective and regioselective copper-catalyzed nitrosoformate dearomatization reaction under aerobic-oxidation conditions.
abstract: An unprecedented copper-catalyzed acylnitroso dearomatization reaction, which expands the traditional acylnitroso ene reaction and acylnitroso Diels-Alder reaction to a new type of transformation, has been developed under aerobic oxidation. Intermolecular and intra-/intermolecular reaction modes demonstrate an entirely different N- or O-acylnitroso selectivity. Hence, we can utilize this reaction as a highly diastereoselective access to a series of new pyrroloindoline derivatives, which are important structural motifs for natural-product synthesis.
authors.affiliation: Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg (Germany), Fax: (+49) 6221-54-4205.
authors.forename: Weibo
authors.initials: W
authors.lastname: Yang
authors.forename: Long
authors.initials: L
authors.lastname: Huang
authors.forename: Yang
authors.initials: Y
authors.lastname: Yu
authors.forename: Daniel
authors.initials: D
authors.lastname: Pflästerer
authors.forename: Frank
authors.initials: F
authors.lastname: Rominger
authors.forename: A Stephen K
authors.initials: AS
authors.lastname: Hashmi
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D009603:Nitroso Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D009603:Nitroso Compounds; D003300:Copper
keywords: aerobic oxidation; copper; dearomatization; nitrosoformate; regioselectivity