TL;DR: A highly enantioselective palladium/l-proline-catalyzed α-arylative desymmetrization of cyclohexanones was developed and led to a series of optically active morphan derivatives bearing α-carbonyl tertiary stereocenters in good yields with excellent enantiOSElectivities.
Abstract: A highly enantioselective palladium/l-proline-catalyzed α-arylative desymmetrization of cyclohexanones was developed. The new strategy for α-arylation reaction led to a series of optically active morphan derivatives bearing α-carbonyl tertiary stereocenters in good yields with excellent enantioselectivities (up to 99% ee).
TL;DR: A review of advances in the synthesis of morphan compounds from 1980 to the present day can be found in this paper, where the authors highlight advances in morphan synthesis from carbocyclic compounds.
Abstract: This review highlights advances in the synthesis of morphan compoundsfrom 1980 to the present day. 1 Introduction 2 Synthetic Approaches from Carbocyclic Compounds 2.1 Aminocyclization Processes Forming the C(1)-NBond 2.1.1 From Amino Alkenes 2.1.2 From Amino Ketones 2.1.3 By Amine Alkylation 2.1.4 By Amino Conjugate Addition upon Enones 2.2 Aminocyclization Processes Forming the N-C(3)Bond 2.3 Cyclization Processes Forming the C(3)-C(4) Bond 2.4 Cyclization Processes Forming the C(4)-C(5) Bond 2.4.1 Aldol Reactions 2.4.2 Piperidine Ring Closure by a Heck Reaction 2.4.3 Alkenylation of Enolates 2.4.4 Radical Cyclizations 2.4.5 Miscellaneous Approaches 3 Synthetic Approaches from Piperidine Derivatives 3.1 Cyclization upon Iminium Ions Forming the C(1)-C(8) Bond 3.2 Cyclization Processes Forming the C(5)-C(6) Bond 3.3 Cyclization Processes Forming the C(6)-C(7) Bond 4 Cascade Processes 5 Rearrangements 6 Synthesis of 5-Phenylmorphans 7 Conclusions
TL;DR: This protocol provides access to highly functionalized 2-azaspiro[4.5]decanes, morphan compounds, and the azatricyclic core of FR901483.
Abstract: Intramolecular Kharasch-type additions of trichloroacetamides on anisole and enol acetates catalyzed by Grubbs’ ruthenium carbenes are described. This protocol provides access to highly functionalized 2-azaspiro[4.5]decanes, morphan compounds, and the azatricyclic core of FR901483.
TL;DR: The six-membered nitrogen-containing ring of the morphan scaffold, ubiquitous in natural products, is formed by an intramolecular aldol process of an aza-tethered dicarbonyl compound, leading to the first asymmetric synthesis of a morphan derivative using organocatalysis.
Abstract: The six-membered nitrogen-containing ring of the morphan scaffold, ubiquitous in natural products, is formed by an intramolecular aldol process of an aza-tethered dicarbonyl compound, leading to the first asymmetric synthesis of a morphan derivative using organocatalysis.
TL;DR: In this article, a partir de la photocyclisation de [chloro-5' methoxy-2' phenoxy]-2 formamido-2" ethyl-3 cyclohexene-2one via une addition de Michael intramoleculaire du (±)-dimethylacetal de la chloro-9 formamidyl-9b methoxy -6 tetrahydro-1,4,4a,9b dibenzofuranne.
Abstract: Synthese a partir de la photocyclisation de [chloro-5' methoxy-2' phenoxy]-2 formamido-2' ethyl-3 cyclohexene-2one via une addition de Michael intramoleculaire du (±)-dimethylacetal de la chloro-9 formamido-2' ethyl-9b methoxy-6 tetrahydro-1,4,4a,9b dibenzofuranne. Analyse RX du compose obtenu. Ce compose ne presente pas l'activite biologique du m-hydroxyphenyl-5 morphane; ceci semble indiquer que l'angle de torsion du cycle phenyl ne convient pas pour cette activite