20047-22-7

Upstream product

• 6640-25-1 4-chlorophenyl cyclopropyl ketone 
• 104-88-1 4-chlorobenzaldehyde 
• 51860-45-8 3-hydroxypropyltriphenylphosphonium bromide 
• 1250907-72-2 methyl (E)-4-(4-chlorophenyl)but-3-enoate 
• 127404-70-0 (E)-4-(4-chlorophenyl)-3-butenoic acid 
• 827605-29-8 2-(4-chloro-phenyl)-5,5-dimethyl-[1,3,2]dioxaborinane 
• 930-22-3 epoxybutene 
• 18228-43-8 (±)-(4-chlorophenyl)(cyclopropyl)methanol 

Downstream Products

• 19967-22-7 4-(p-chlorophenyl)-1-butanol 
• 1426692-57-0 3-chloro-2-(4-chlorophenyl)tetrahydrofuran 

Relevant academic research and scientific papers

An Enzymatic Platform for the Highly Enantioselective and Stereodivergent Construction of Cyclopropyl-δ-lactones

Abiological enzymes offers new opportunities for sustainable chemistry. Herein, we report the development of biological catalysts derived from sperm whale myoglobin that exploit a carbene transfer mechanism for the asymmetric synthesis of cyclopropane-fused-δ-lactones, which are key structural motifs found in many biologically active natural products. While hemin, wild-type myoglobin, and other hemoproteins are unable to catalyze this reaction, the myoglobin scaffold could be remodeled by protein engineering to permit the intramolecular cyclopropanation of a broad spectrum of homoallylic diazoacetate substrates in high yields and with up to 99 % enantiomeric excess. Via an alternate evolutionary trajectory, a stereodivergent biocatalyst was also obtained for affording mirror-image forms of the desired bicyclic products. In combination with whole-cell transformations, the myoglobin-based biocatalyst was used for the asymmetric construction of a cyclopropyl-δ-lactone scaffold at a gram scale, which could be further elaborated to furnish a variety of enantiopure trisubstituted cyclopropanes.

Synthesis method of aryl-substituted homoallylic alcohol

The invention relates to compound preparation, belongs to the field of organic synthesis and discloses a synthesis method of aryl-substituted homoallylic alcohol. An aryl boron compound and alkenyl epoxy serve as raw materials to react in a solvent under

Cu-catalyzed cross-coupling reactions of vinyl epoxide with organoboron compounds: access to homoallylic alcohols

Copper-catalyzed cross-coupling reactions of vinyl epoxide with arylboronates to obtain aryl-substituted homoallylic alcohols are described. The reaction selectivity was different to that of previously reported vinyl epoxide ring-opening reactions using aryl nucleophiles. The reaction proceeded under mild conditions, affording aryl-substituted homoallylic alcohols with high selectivity and in good to excellent yields. The reaction provides convenient access to aryl-substituted homoallylic alcohols from vinyl epoxide.

Nickel Catalyzed Regio-, Diastereo-, and Enantioselective Cross-Coupling of 3,4-Epoxyalcohol with Aryl Iodides

The first catalytic, regioselective cross-coupling of 3,4-epoxyalcohol with aryl iodides is reported. The combination of NiCl2·DME and a newly developed C2-symmetric oxazoline ligand plays a key role in selective ring opening of seve

Copper-Catalyzed Diastereoselective Synthesis of Trifluoromethylated Tetrahydrofurans

The copper-catalyzed intramolecular diastereoselective trifluoromethylcycloetherification of homoallylic alcohols with Togni's reagent as trifluoromethylating reagent was realized under mild conditions. Various trifluoromethylated tetrahydrofurans were synthesized in moderate to good yields. Moreover, a wide range of common functional groups was tolerated.

Hot water-promoted cyclopropylcarbinyl rearrangement facilitates construction of homoallylic alcohols

In refluxing 9 : 1 (v/v) H2O-1,4-dioxane and without an additional catalyst, the rearrangements of various types of cyclopropyl carbinols were attempted. It was found that the reactions generally gave homoallylic alcohols in good to very high chemical yields. Rearrangements of bicyclic or tricyclic cyclopropyl carbinols readily gave the desired ring-expanded cyclic homoallylic alcohols which are difficult to synthesize by other means.

Asymmetric 5-endo chloroetherification of homoallylic alcohols toward the synthesis of chiral β-chlorotetrahydrofurans

An asymmetric 5-endo chloroetherification of homoallylic alcohols is successfully developed that employs an easily available quaternary ammonium salt derived from cinchonine as a conventional organocatalyst. This approach provides ready access to β-chloro