A Practical Protocol for the Highly <i>E</i>-Selective Formation of Aryl-Substituted Silylketene Acetals

Harker, Wesley R. R.; Carswell, Emma L.; Carbery, David R.

doi:10.1021/ol101580y

Cited by 17 publications

(12 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Preparation of substrates (1a, 1f-1p, 4a-4f, 6a and 6b). [25][26] To a solution of DCC (2.1 g, 10 mmol, 1.0 equiv) in DCM (50 mL) at 0 o C was added DMAP (1.5 g, 12 mmol, 1.2 equiv) and 2-(4-methoxyphenyl) acetic acid (1.7 g, 10 mmol, 1.0 equiv). To the resulting suspension was then added 1,3-dimethoxy-2-propanol (1.8 g, 15 mmol, 1.5 equiv).…”

Section: Preparation Of Directing Group (1b-1e)mentioning

confidence: 99%

Palladium-Catalyzed ortho-Olefination of Phenyl Acetic and Phenyl Propylacetic Esters via C–H Bond Activation

Guan

Han

et al. 2015

J. Org. Chem.

View full text Add to dashboard Cite

A highly regioselective palladium-catalyzed ester-directed ortho-olefination of phenyl acetic and propionic esters with olefins via C-H bond activation has been developed. A wide variety of phenyl acetic and propionic esters were tolerated in this transformation, affording the corresponding olefinated aromatic compounds. The ortho-olefination of heterocyclic acetic and propionic esters also took place smoothly giving the products in good yields, thus proving the potential utility of this protocol in synthetic chemistry.

show abstract

Section: Preparation Of Directing Group (1b-1e)mentioning

confidence: 99%

Palladium-Catalyzed ortho-Olefination of Phenyl Acetic and Phenyl Propylacetic Esters via C–H Bond Activation

Guan

Han

et al. 2015

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…Enamines 3 were synthesized from acetophenone and morpholine 13 . Diazo compounds were prepared according to the literature 12 23 . Aldimines 4 were prepared from condensation of the corresponding aldehydes with arylamines according to the reported methods 24 .…”

Section: Methodsmentioning

confidence: 99%

Bond cleavage, fragment modification and reassembly in enantioselective three-component reactions

et al. 2015

View full text Add to dashboard Cite

Chemical bond cleavage and reconstruction are common processes in traditional rearrangement reactions. In contrast, the process that involves bond cleavage, fragment modification and then reconstruction of the modified fragment provides an efficient way to build structurally diversified molecules. Here, we report a palladium(II)/chiral phosphoric acid catalysed three-component reaction of aryldiazoacetates, enamines and imines to afford α-amino-δ-oxo pentanoic acid derivatives in good yields with excellent diastereoselectivities and high enantioselectivities. The stereoselective reaction went through a unique process that involves cleavage of a C–N bond, modification of the resulting amino fragment and selective reassembly of the modified fragment. This innovative multi-component process represents a highly efficient way to build structurally diversified polyfunctional molecules in an atom and step economic fashion. A keto-iminium is proposed as a key intermediate and a chiral palladium/phosphate complex is proposed as an active catalyst.

show abstract

“…The spectral data were consistent with reported values. 47 mg, 0.57 mmol) was reacted according to the general procedure. Methyl ester 3n was isolated as a clear, colorless oil (82 mg, 76% yield).…”

Section: Scheme 1 Chemoselective Esterificationmentioning

confidence: 99%

Catalytic Methyl Transfer from Dimethylcarbonate to Carboxylic Acids

Sweeney

Zoglio

et al. 2013

J. Org. Chem.

View full text Add to dashboard Cite

Although methylation reactions are commonplace, currently used reagents are hazardous, toxic, and/or unstable. Dimethylcarbonate has been put forth as an inexpensive, nontoxic, and "green" potential methylating reagent. Herein we report a general, base-catalyzed methyl transfer from dimethylcarbonate to carboxylic acids. High selectivity for esterification is observed even in the presence of unprotected phenols, and the mild reaction conditions enable conservation of stereochemistry at epimerizable stereocenters. Isotope-labeling studies suggest a mechanism proceeding by direct methyl transfer from dimethylcarbonate to the substrate.

show abstract

A Practical Protocol for the Highly E-Selective Formation of Aryl-Substituted Silylketene Acetals

Cited by 17 publications

References 31 publications

Palladium-Catalyzed ortho-Olefination of Phenyl Acetic and Phenyl Propylacetic Esters via C–H Bond Activation

Palladium-Catalyzed ortho-Olefination of Phenyl Acetic and Phenyl Propylacetic Esters via C–H Bond Activation

Bond cleavage, fragment modification and reassembly in enantioselective three-component reactions

Catalytic Methyl Transfer from Dimethylcarbonate to Carboxylic Acids

Contact Info

Product

Resources

About