Terminal olefins to chromans, isochromans, and pyrans via allylic C-H oxidation.

PubWeight™: 0.79‹?›

🔗 View Article (PMC 4132955)

Published in J Am Chem Soc on July 16, 2014

Authors

Stephen E Ammann1, Grant T Rice, M Christina White

Author Affiliations

1: Roger Adams Laboratory, Department of Chemistry, University of Illinois at Urbana-Champaign , Urbana, Illinois 61801, United States.

Articles cited by this

Understanding and exploiting C-H bond activation. Nature (2002) 4.48

Serial ligand catalysis: a highly selective allylic C-H oxidation. J Am Chem Soc (2005) 1.89

Synthesis of heterocycles via palladium-catalyzed oxidative addition. Chem Rev (2006) 1.68

On the interpretation of deuterium kinetic isotope effects in C-H bond functionalizations by transition-metal complexes. Angew Chem Int Ed Engl (2012) 1.61

Transition metal-catalyzed C-H activation reactions: diastereoselectivity and enantioselectivity. Chem Soc Rev (2009) 1.61

Chemistry. Adding aliphatic C-H bond oxidations to synthesis. Science (2012) 1.56

Oxidative cyclizations in a nonpolar solvent using molecular oxygen and studies on the stereochemistry of oxypalladation. J Am Chem Soc (2005) 1.55

Catalytic intermolecular linear allylic C-H amination via heterobimetallic catalysis. J Am Chem Soc (2008) 1.54

Macrolactonization via hydrocarbon oxidation. J Am Chem Soc (2006) 1.42

Intra/intermolecular direct allylic alkylation via Pd(II)-catalyzed allylic C-H activation. J Am Chem Soc (2008) 1.26

The synthesis of chromenes, chromanes, coumarins and related heterocycles via tandem reactions of salicylic aldehydes or salicylic imines with alpha,beta-unsaturated compounds. Org Biomol Chem (2007) 1.20

Catalytic intermolecular allylic C-H alkylation. J Am Chem Soc (2008) 1.15

Selective functionalisation of saturated C-H bonds with metalloporphyrin catalysts. Chem Soc Rev (2011) 1.15

A catalytic, Brønsted base strategy for intermolecular allylic C-H amination. J Am Chem Soc (2009) 1.10

A chiral Lewis acid strategy for enantioselective allylic C-H oxidation. Angew Chem Int Ed Engl (2008) 1.07

Allylic C-H amination for the preparation of syn-1,3-amino alcohol motifs. J Am Chem Soc (2009) 1.04

Synthesis of chiral chromans by the Pd-catalyzed asymmetric allylic alkylation (AAA): scope, mechanism, and applications. J Am Chem Soc (2004) 1.02

Palladium-catalyzed allylic C-H fluorination. J Am Chem Soc (2013) 0.97

C-H bond activation by [{(diimine)Pd(mu-OH)}2]2+ dimers: mechanism-guided catalytic improvement. Angew Chem Int Ed Engl (2008) 0.96

Unusual effects in the pd-catalyzed asymmetric allylic alkylations: synthesis of chiral chromans. J Am Chem Soc (2003) 0.93

Synthetic versatility in C-H oxidation: a rapid approach to differentiated diols and pyrans from simple olefins. J Am Chem Soc (2011) 0.83

Synthesis of chromans via Pd-catalyzed alkene carboetherification reactions. Chem Commun (Camb) (2011) 0.83

Catalyst-controlled C-O versus C-N allylic functionalization of terminal olefins. J Am Chem Soc (2013) 0.83

An Asymmetric Synthesis of C-2-epi-Hygromycin A We thank the National Science Foundation and the National Institute of Health, General Medical Sciences, for their generous support of our programs. O.D. thanks the Association pour la Recherche contre le Cancer (ARC) for a postdoctoral fellowship. Mass spectra were kindly provided by the Mass Spectrometry Facility, University of San Francisco, supported by the NIH Division of Research Resources. Angew Chem Int Ed Engl (2001) 0.82

Palladium(II)-catalyzed enantioselective synthesis of 2-vinyl oxygen heterocycles. J Org Chem (2012) 0.81

Novel sigma receptor ligands. Part 2. SAR of spiro[[2]benzopyran-1,4'-piperidines] and spiro[[2]benzofuran-1,4'-piperidines] with carbon substituents in position 3. J Med Chem (2002) 0.80

Articles by these authors

A predictably selective aliphatic C-H oxidation reaction for complex molecule synthesis. Science (2007) 3.94

Serial ligand catalysis: a highly selective allylic C-H oxidation. J Am Chem Soc (2005) 1.89

Combined effects on selectivity in Fe-catalyzed methylene oxidation. Science (2010) 1.88

A sulfoxide-promoted, catalytic method for the regioselective synthesis of allylic acetates from monosubstituted olefins via C-H oxidation. J Am Chem Soc (2004) 1.75

Catalytic intermolecular linear allylic C-H amination via heterobimetallic catalysis. J Am Chem Soc (2008) 1.54

Hydrocarbon oxidation vs C-C bond-forming approaches for efficient syntheses of oxygenated molecules. Org Lett (2005) 1.50

Total synthesis and study of 6-deoxyerythronolide B by late-stage C-H oxidation. Nat Chem (2009) 1.49

syn-1,2-Amino alcohols via diastereoselective allylic C-H amination. J Am Chem Soc (2007) 1.47

A general and highly selective chelate-controlled intermolecular oxidative Heck reaction. J Am Chem Soc (2008) 1.43

Macrolactonization via hydrocarbon oxidation. J Am Chem Soc (2006) 1.42

Sequential hydrocarbon functionalization: allylic C-H oxidation/vinylic C-H arylation. J Am Chem Soc (2006) 1.36

Molecular complexity via C-H activation: a dehydrogenative Diels-Alder reaction. J Am Chem Soc (2011) 1.35

Catalyst-controlled aliphatic C-H oxidations with a predictive model for site-selectivity. J Am Chem Soc (2013) 1.21

Polyol synthesis through hydrocarbon oxidation: de novo synthesis of L-galactose. Angew Chem Int Ed Engl (2006) 1.17

Iron-catalyzed intramolecular allylic C-H amination. J Am Chem Soc (2012) 1.16

Catalytic intermolecular allylic C-H alkylation. J Am Chem Soc (2008) 1.15

A catalytic, Brønsted base strategy for intermolecular allylic C-H amination. J Am Chem Soc (2009) 1.10

A chiral Lewis acid strategy for enantioselective allylic C-H oxidation. Angew Chem Int Ed Engl (2008) 1.07

Allylic C-H amination for the preparation of syn-1,3-amino alcohol motifs. J Am Chem Soc (2009) 1.04

Diverting non-haem iron catalysed aliphatic C-H hydroxylations towards desaturations. Nat Chem (2011) 1.03

Synthesis of complex allylic esters via C-H oxidation vs C-C bond formation. J Am Chem Soc (2010) 0.96

Allylic C-H alkylation of unactivated α-olefins: serial ligand catalysis resumed. Angew Chem Int Ed Engl (2011) 0.96

Directed metal (oxo) aliphatic C-H hydroxylations: overriding substrate bias. J Am Chem Soc (2012) 0.88

On the macrocyclization of the erythromycin core: preorganization is not required. Angew Chem Int Ed Engl (2011) 0.87

Cafestol to Tricalysiolide B and Oxidized Analogues: Biosynthetic and Derivatization Studies Using Non-heme Iron Catalyst Fe(PDP). Synlett (2012) 0.84

Diversification of a β-Lactam Pharmacophore via Allylic C-H Amination: Accelerating Effect of Lewis Acid Co-Catalyst. Tetrahedron (2010) 0.83

Synthetic versatility in C-H oxidation: a rapid approach to differentiated diols and pyrans from simple olefins. J Am Chem Soc (2011) 0.83

Catalyst-controlled C-O versus C-N allylic functionalization of terminal olefins. J Am Chem Soc (2013) 0.83

Terminal olefins to linear α,β-unsaturated ketones: Pd(II)/hypervalent iodine co-catalyzed Wacker oxidation-dehydrogenation. J Am Chem Soc (2013) 0.82

N-Boc amines to oxazolidinones via Pd(II)/bis-sulfoxide/Brønsted acid co-catalyzed allylic C-H oxidation. J Am Chem Soc (2014) 0.81

General allylic C-H alkylation with tertiary nucleophiles. J Am Chem Soc (2014) 0.78

Oxidative Heck vinylation for the synthesis of complex dienes and polyenes. J Am Chem Soc (2013) 0.78

Sequential allylic C-H amination/vinylic C-H arylation: a strategy for unnatural amino acid synthesis from α-olefins. Org Lett (2012) 0.77