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The stereoselective synthesis of cis-disubstituted cyclopropanes by the Au(I)/PPh3-catalyzed cycloaddition of propargylic esters and styrene has been studied using density functional theory calculations. The computed mechanistic scheme involves the rate-limiting 1,2-rearrangement of the propargylic ester with the π-coordinated gold complex, followed by the (2+1)-cheletropic reaction of styrene with the alkenyl-Au(I) carbene intermediate to afford the cis-disubstituted cyclopropane derivative in a high cis/trans diastereomeric ratio. With (R)-di-chloro,di-gold-SEGPHOS complex as catalyst, computations are consistent with a rate-determining (2+1)-cheletropic reaction, in which facial discrimination is proposed to result from a combination of subtle steric and electronic effects in the SiRe facial approach transition structure, which favor the formation of the cis-cyclopropane diastereomer of 1R,2S absolute configuration, as experimentally observed.
This article was published in the following journal.
Name: The Journal of organic chemistry
The controlled syndiospecific polymerization of three Si-H-containing styrenes, that is, 4-(methylhydrosilyl)styrene (FSt-1), 4-(dimethylhydrosilyl)styrene (FSt-2) and 4-(diisopropylhydrosilyl)styrene...
Theoretical studies have been undertaken to rationalize the origin of the enantioselective Diels-Alder reaction (DA) of O-hydroxylstyrene and azlactone catalyzed by (a) chiral BINOL-phosphoric acid (C...
An unusual hybrid palladium catalyst containing an anionic chiral Co(III) complex and a chiral phosphoramidite ligand shows high capacity of catalyzing the asymmetric thioamide-directed C(sp3)-H aryla...
This study demonstrates for the first time that styrene oligomers (SOs), which are indicators of polystyrene (PS) plastic contamination in the environment, are transported from land to the ocean. Samp...
Plastic injection industry workers are exposed to toxic gases and vapors, including styrene. This study aimed to measure exposure to styrene and its relation with urine mandelic acid among plastics in...
Infrapyloric artery(IPA) is of great importance for gastric cancer patients. According to previous study, the origin of IPA varies greatly among different studies. This trial aims to tell ...
Autistic spectrum disorders (ASD) are highly debilitating developmental syndromes which core feature is social and communications disorders. Motor skill impairments are frequently describe...
Fever of unknown origin (FUO) and biologic inflammatory syndrome of unknown origin (SII) are two frequent causes of hospitalization or consultation in infectious disease unit and internal ...
The pathworks tissue of origin test is a microarray-based test with the goal of identifying the tissue of origin in patients with metastatic tumors of unknown primary site.
This study is designed to evaluate the value of tissue-of-origin (ORIGIN-PanCA○R) profiling in predicting primary site and directing therapy in patients with cancer of unknown primary.
The study of ancient inscriptions and modes of writing. It includes the deciphering of manuscripts and other forms to determine their date, provenance, etc. (Webster's 1st ed)
A colorless, toxic liquid with a strong aromatic odor. It is used to make rubbers, polymers and copolymers, and polystyrene plastics.
Techniques for standardizing and expediting taxonomic identification or classification of organisms that are based on deciphering the sequence of one or a few regions of DNA known as the "DNA barcode".
Derivatives and polymers of styrene. They are used in the manufacturing of synthetic rubber, plastics, and resins. Some of the polymers form the skeletal structures for ion exchange resin beads.
Polymerized forms of styrene used as a biocompatible material, especially in dentistry. They are thermoplastic and are used as insulators, for injection molding and casting, as sheets, plates, rods, rigid forms and beads.