1217263-84-7

Upstream product

• 5747-06-8 4-phenylpent-4-enoic acid 
• 2051-95-8 succinylbenzene 
• 93863-05-9 4-phenylpent-4-enoic acid methyl ester 
• 25333-24-8 3-benzoylpropionic acid methyl ester 

Downstream Products

• 1229618-00-1 3-(2-phenyloxiran-2-yl)propan-1-ol 

Relevant academic research and scientific papers

A Catalyst-Controlled Enantiodivergent Bromolactonization

A catalyst-controlled enantiodivergent bromolactonization of olefinic acids has been developed. Quinine-derived amino-amides bearing the same chiral core but different achiral aryl substituents were used as the catalysts. Switching the methoxy substituent in the aryl amide system from meta- to ortho-position results in a complete switch in asymmetric induction to afford the desired lactone in good enantioselectivity and yield. Mechanistic studies, including chemical experiments and density functional theory calculations, reveal that the differences in steric and electronic effects of the catalyst substituent alter the reaction mechanism.

Synthesis of Novel C 2-Symmetric Sulfur-Based Catalysts: Asymmetric Formation of Halo- and Seleno-Functionalized Normal- and Medium-Sized Rings

The synthesis of novel, highly functionalized, C 2 -symmetric sulfur-based catalysts is developed and their catalytic applications are explored in asymmetric bromo-, iodo- and seleno-functionalizations of alkenoic acids. This protocol provides

Enantioselective Halolactonization Reactions using BINOL-Derived Bifunctional Catalysts: Methodology, Diversification, and Applications

A general protocol is described for inducing enantioselective halolactonizations of unsaturated carboxylic acids using novel bifunctional organic catalysts derived from a chiral binaphthalene scaffold. Bromo- and iodolactonization reactions of diversely substituted, unsaturated carboxylic acids proceed with high degrees of enantioselectivity, regioselectivity, and diastereoselectivity. Notably, these BINOL-derived catalysts are the first to induce the bromo- and iodolactonizations of 5-alkyl-4(Z)-olefinic acids via 5-exo mode cyclizations to give lactones in which new carbon-halogen bonds are created at a stereogenic center with high diastereo- and enantioselectivities. Iodolactonizations of 6-substituted-5(Z)-olefinic acids also occur via 6-exo cyclizations to provide δ-lactones with excellent enantioselectivities. Several notable applications of this halolactonization methodology were developed for desymmetrization, kinetic resolution, and epoxidation of Z-alkenes. The utility of these reactions is demonstrated by their application to a synthesis of precursors of the F-ring subunit of kibdelone C and to the shortest catalytic, enantioselective synthesis of (+)-disparlure reported to date.

C2-symmetric cyclic selenium-catalyzed enantioselective bromoaminocyclization

A catalytic asymmetric bromocyclization of trisubstituted olefinic amides that uses a C2-symmetric mannitol-derived cyclic selenium catalyst and a stoichiometric amount of N-bromophthalimide is reported. The resulting enantioenriched pyrrolidine products, which contain two stereogenic centers, can undergo rearrangement to yield 2,3-disubstituted piperidines with excellent diastereoselectivity and enantiospecificity.

Catalytic asymmetric bromolactonization reactions using (DHQD) 2PHAL-benzoic acid combinations

Catalytic (DHQD)2PHAL as modified by added benzoic acid, is an off-the-shelf catalyst-additive combination for effecting catalytic asymmetric bromolactonization reactions. This combination delivers bromolactones with asymmetric induction at a c

Enantioselective bromolactonization using an S-alkyl thiocarbamate catalyst

The apple never falls far from the tree: S-alkyl thiocarbamate 1 (see scheme, NBP=N-bromophthalimide) was prepared in high yield through a synthetic sequence involving a Newman-Kwart rearrangement of the corresponding O-alkyl thiocarbamates. Compound 1 was used to catalyze bromolactonization, thus providing enantioenriched δ-lactones in excellent yield and enantioselectivity. Copyright

Bifunctional catalyst promotes highly enantioselective bromolactonizations to generate stereogenic C-Br bonds

A novel bifunctional catalyst derived from BINOL has been developed that promotes the highly enantioselective bromolactonizations of a number of structurally distinct unsaturated acids. Like some known catalysts, this catalyst promotes highly enantioselec

Catalytic enantioselective halolactonization of enynes and Alkenes

New organocatalysts have been developed for the enantioselective halolactonization of (Z)-1,3-enynes and 1,1-disubstituted alkenes. In the case of 1,3-enynes, the carboxylate nucleophile and halogen electrophile were added to the conjugated π-system from the same face. Up to 99%ee was achieved for the 1,4-syn-bromolactonization of conjugated (Z)-1,3-enynes. Based on the results from the enyne halolactonization, a second generation of catalysts was designed for simple olefins. Up to 91%ee was observed for chlorolactonization of 1,1-disubstituted alkenes. The catalysts developed for the enantioselective halolactonization of both enynes and alkenes are composed of a cinchona alkaloid skeleton tethered to a urea group.

Catalytic enantioselective bromolactonization of alkenoic acids in the presence of palladium complexes

The catalytic enantioselective bromolactonization of alkenoic acids promoted by chiral palladium complexes has been developed, allowing facile synthesis of the corresponding γ-lactones with excellent enantioselectivity (up to 97% ee). The method reported

A peptide bromoiodinane approach for asymmetric bromolactonization

A series of 37 peptides containing an iodo-aryl amide active site were generated by means of both solid phase and conventional synthesis. These peptides were screened for asymmetric induction in the bromolactonization of 4-phenyl-4-pentenoic acid based on the generation of chiral bromoiodinane bromenium sources. The study culminated in the discovery of a tri-peptide iodo-aryl amide that effected the desired bromolactonization in quantitative conversion with 24% ee. The experiments disclosed herein provided valuable insight that ultimately facilitated the development of more synthetically useful enantioselective halocyclization methodology.