Intramolecular aminopalladation of alkenes as a key step to pyrrolidines and related heterocycles.

PubWeight™: 1.16‹?› | Rank: Top 10%

🔗 View Article (PMID 17576481)

Published in Chem Soc Rev on February 28, 2007

Authors

Ana Minatti1, Kilian Muñiz

Author Affiliations

1: Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave., Cambridge, Massachusetts 02139, USA.

Articles citing this

Asymmetric palladium-catalyzed carboamination reactions for the synthesis of enantiomerically enriched 2-(arylmethyl)- and 2-(alkenylmethyl)pyrrolidines. J Am Chem Soc (2010) 1.49

Mild conditions for Pd-catalyzed carboamination of N-protected hex-4-enylamines and 1-, 3-, and 4-substituted pent-4-enylamines. Scope, limitations, and mechanism of pyrrolidine formation. J Org Chem (2008) 1.33

Reversible alkene insertion into the Pd-N bond of Pd(II)-sulfonamidates and implications for catalytic amidation reactions. J Am Chem Soc (2011) 1.03

Reconciling the stereochemical course of nucleopalladation with the development of enantioselective wacker-type cyclizations. Angew Chem Int Ed Engl (2012) 1.03

Mechanistic studies of Wacker-type intramolecular aerobic oxidative amination of alkenes catalyzed by Pd(OAc)2/pyridine. J Org Chem (2011) 0.97

Stereoselective Copper-Catalyzed Intramolecular Alkene Aminooxygenation: Effects of Substrate and Ligand Structure on Selectivity. European J Org Chem (2011) 0.96

Mechanistic studies of Wacker-type amidocyclization of alkenes catalyzed by (IMes)Pd(TFA)2(H2O): kinetic and stereochemical implications of proton transfer. J Org Chem (2012) 0.93

Alkylgold complexes by the intramolecular aminoauration of unactivated alkenes. Chem Sci (2010) 0.92

Methods for direct alkene diamination, new & old. Tetrahedron (2012) 0.92

Intramolecular Pd(II)-catalyzed aerobic oxidative amination of alkenes: synthesis of six-membered N-heterocycles. Org Lett (2012) 0.91

Palladium-catalyzed intermolecular aminoacetoxylation of alkenes and the influence of PhI(OAc)2 on aminopalladation stereoselectivity. J Org Chem (2013) 0.90

Mechanistic Studies of Azaphilic versus Carbophilic Activation by Gold(I) in the Gold/Palladium Dual-Catalyzed Rearrangement of Alkenyl Vinyl Aziridines. Organometallics (2012) 0.89

Palladium-catalyzed alkene carboamination reactions for the synthesis of substituted piperazines. Tetrahedron (2009) 0.88

Palladium-catalyzed 1,1-aryloxygenation of terminal olefins. Org Lett (2011) 0.87

Pd(0)-catalyzed sequential C-N bond formation via allylic and aromatic C-H amination of α-methylstyrenes with diaziridinone. Org Lett (2013) 0.78

Diazafluorenone-Promoted Oxidation Catalysis: Insights into the Role of Bidentate Ligands in Pd-Catalyzed Aerobic Aza-Wacker Reactions. ACS Catal (2016) 0.77

Stereoselective synthesis of cis-2,5-disubstituted pyrrolidines via Wacker-type aerobic oxidative cyclization of alkenes with tert-butanesulfinamide nucleophiles. Org Lett (2012) 0.77

Stereoselective Synthesis of Saturated Heterocycles via Pd-Catalyzed Alkene Carboetherification and Carboamination Reactions. Synlett (2006) 0.76

Direct access to pyrido/pyrrolo[2,1-b]quinazolin-9(1H)-ones through silver-mediated intramolecular alkyne hydroamination reactions. Beilstein J Org Chem (2015) 0.75

Palladium-catalyzed one-step synthesis of isoindole-1,3-diones by carbonylative cyclization of o-halobenzoates and primary amines. J Org Chem (2008) 0.75

Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction. J Am Chem Soc (2016) 0.75

Articles by these authors

Palladium(II)-catalyzed intramolecular diamination of unfunctionalized alkenes. J Am Chem Soc (2005) 2.04

trans-RuH(eta1-BH4)(binap)(1,2-diamine): a catalyst for asymmetric hydrogenation of simple ketones under base-free conditions. J Am Chem Soc (2002) 1.28

Mechanism of asymmetric hydrogenation of ketones catalyzed by BINAP/1,2-diamine-rutheniumII complexes. J Am Chem Soc (2003) 1.20

Direct synthesis of bicyclic guanidines through unprecedented palladium(ii) catalysed diamination with copper chloride as oxidant. Chem Commun (Camb) (2008) 1.18

Catalyzed Asymmetric Arylation Reactions. Angew Chem Int Ed Engl (2001) 1.13

Oxidative interception of the hydroamination pathway: a gold-catalyzed diamination of alkenes. Chemistry (2009) 1.07

Metal-ligand bifunctional catalysis for asymmetric hydrogenation. Philos Trans A Math Phys Eng Sci (2005) 0.93

An intermolecular palladium-catalyzed diamination of unactivated alkenes. Angew Chem Int Ed Engl (2010) 0.92

Enantioselective metal-free diamination of styrenes. Angew Chem Int Ed Engl (2011) 0.92

Palladium-catalyzed intermolecular aminoacetoxylation of alkenes and the influence of PhI(OAc)2 on aminopalladation stereoselectivity. J Org Chem (2013) 0.90

Metal-free iodine(III)-promoted direct intermolecular C-H amination reactions of acetylenes. J Am Chem Soc (2012) 0.86

Defined hypervalent iodine(III) reagents incorporating transferable nitrogen groups: nucleophilic amination through electrophilic activation. Angew Chem Int Ed Engl (2012) 0.86

Asymmetric hydrogenation of tert-alkyl ketones. J Am Chem Soc (2005) 0.85

Palladium-catalyzed vicinal difunctionalization of internal alkenes: diastereoselective synthesis of diamines. Angew Chem Int Ed Engl (2012) 0.85

Palladium-catalyzed intermolecular C(sp3)-H amidation. Angew Chem Int Ed Engl (2012) 0.83

Vicinal difunctionalization of alkenes with iodine(III) reagents and catalysts. Chem Asian J (2014) 0.82

Iodine(III)-promoted intermolecular diamination of alkenes. Chem Asian J (2012) 0.79

Indole synthesis based on a modified Koser reagent. Angew Chem Int Ed Engl (2014) 0.79

An approach to the regioselective diamination of conjugated di- and trienes. Chemistry (2012) 0.78

Palladium-catalyzed intramolecular diamination of acrylic esters using sulfamates as nitrogen source. J Org Chem (2012) 0.78

Oxidative diamination promoted by dinuclear iodine(III) reagents. Org Lett (2013) 0.76

Iodine(III)-mediated intermolecular allylic amination under metal-free conditions. J Am Chem Soc (2012) 0.76

Polymer-supported ferrocenyl oxazolines for the catalyzed highly enantioselective phenyl transfer to aldehydes. Bioorg Med Chem Lett (2002) 0.76

Comparison of free energy surfaces calculations from ab initio molecular dynamic simulations at the example of two transition metal catalyzed reactions. Int J Mol Sci (2011) 0.75

Road maps for nitrogen-transfer catalysis: the challenge of the osmium(VIII)-catalyzed diamination. Chemistry (2004) 0.75

An electrophilic cleavage procedure for the asymmetric dihydroxylation: direct enantioselective synthesis of cyclic boronic esters from olefins. Chemistry (2005) 0.75

Pd-N to Pd-O rearrangement for a carbamate synthesis from carbon dioxide and methane: a density functional and ab initio molecular dynamics metadynamics study. Angew Chem Int Ed Engl (2011) 0.75

First osmium-catalysed ketamination of alkenes. Chem Commun (Camb) (2005) 0.75

Hypervalent iodine mediated oxidative amination of allenes. Org Lett (2014) 0.75

Synthesis of small tripeptide molecules through a catalysis sequence comprising metathesis and aminohydroxylation. Chemistry (2006) 0.75