1194019-99-2

Upstream product

• 103729-80-2 2-methyl-1-phenylprop-2-en-1-ol 
• 78-39-7 Triethyl orthoacetate 
• 673-32-5 1-Phenylprop-1-yne 
• 140-88-5 ethyl acrylate 
• 83126-03-8 (E)-(2-Methyl-3-phenyl-2-propenyl)malonsaeure-diethylester 
• 1507-88-6 <(E)-3-chloro-2-methyl-1-propenyl>benzene 
• 1504-55-8 (E)-3-phenyl-2-methyl-2-propenol 

Downstream Products

• 1393706-24-5 ethyl (E)-2-(2'-hydroxyprop-2'-yl)-4-methyl-5-phenyl-4-pentenoate 
• 1453416-45-9 C₁₅H₁₈O₂ 
• 83126-04-9 (4E)-4-methyl-5-phenylpent-4-enoic acid 
• 57919-03-6 (E)-4-Methyl-5-phenyl-4-penten-1-ol 
• 1380523-17-0 (E)-dimethyl 2-(4-methyl-5-phenylpent-4-enyl)malonate 
• 1380523-58-9 (E)-4-methyl-5-phenylpent-4-enyl methanesulfonate 

Relevant academic research and scientific papers

Visible-Light-Driven Intermolecular Reductive Ene–Yne Coupling by Iridium/Cobalt Dual Catalysis for C(sp3)?C(sp2) Bond Formation

A new methodology to form C(sp3)?C(sp2) bonds by visible-light-driven intermolecular reductive ene–yne coupling has been successfully developed. The process relies on the ability of the Hantzsch ester to contribute in both SET and HAT processes through a unified cobalt and iridium catalytic system. This procedure avoids the use of stoichiometric amounts of reducing metallic reagents, which is translated into high functional-group tolerance and atom economy.

A Sequential Acyl Thiol-Ene and Thiolactonization Approach for the Synthesis of δ-Thiolactones

A novel strategy for the synthesis of δ-thiolactones from inexpensive and readily available ?-unsaturated esters has been developed. This strategy incorporates a radical acyl thiol-ene reaction as the key C-S bond forming step. Cyclization is achieved via a Steglich-type thiolactonization of 5-mercaptopentanoic acids. We report the facile and scalable synthesis of δ-thiolactones in moderate to good yield under mild reaction conditions with tolerance for a range of functional groups.

Photoredox/Cobalt Dual Catalysis for Visible-Light-Mediated Alkene-Alkyne Coupling

Dual photoredox transition-metal catalysis has recently emerged as a powerful tool for making synthetically challenging carbon-carbon bonds under milder reaction conditions. Herein, we report on the visible-light-mediated controlled generation of low-valent cobalt catalyst without the need for a metallic reductant. It enabled C-C bond formation via ene-yne coupling at room temperature. The generality of this dual catalysis is demonstrated via the creation of sizable molecular diversity with the accommodation of several functional groups.

Stereospecific Alkene Aziridination Using a Bifunctional Amino-Reagent: An Aza-Prilezhaev Reaction

In situ deprotection (TFA) of O-Ts activated N-Boc hydroxylamines triggers intramolecular aziridination of N-tethered alkenes to provide complex N-heterocyclic ring systems. Synthetic and computational studies corroborate a diastereospecific aza-Prilezhaev-type mechanism. The feasibility of related intermolecular alkene aziridinations is also demonstrated.

Study on the total synthesis of velbanamine: Chemoselective dioxygenation of alkenes with PIFA via a stop-and-flow strategy

A "stop-and-flow" strategy was developed for the chemoselective dioxygenation of alkenes with a PIFA-initiated cyclization. This method is conceived for the desymmetrization of seco-diene, and a series of substituted 5-hydroxymethyl-γ-lactones were constructed after hydrolysis. This strategy also differentiates terminally substituted alkenes and constitutes a potentially novel synthetic approach for the efficient synthesis toward velbanamine.

Manganese(III) acetate mediated oxidative radical cyclizations. Toward vicinal all-carbon quaternary stereocenters

Manganese(III) acetate mediated oxidative radical cyclizations have been used to synthesize a range of densely functionalized and sterically congested cyclopentane-lactones. A number of the resulting lactones contain vicinal all-carbon quaternary stereocenters adjacent to a tertiary benzylic stereocenter and are formed with high levels of stereocontrol.

Controlling 6-endo-selectivity in oxidation/bromocyclization cascades for synthesis of aplysiapyranoids and other 2,2,6,6-substituted tetrahydropyrans

A cascade, composed of (i) oxovanadium(V)-catalyzed oxidation of bromide by tert-butyl hydroperoxide and (ii) stereoselective 6-endo-bromocyclization, affords 3-bromo-2-aryl-2,6,6-trimethyltetrahydropyrans from styrene-type tertiary alkenols in synthetically useful yields. (E)-Alkenols add the bromo- and the alkoxy substituent anti-selectively across the double bond, indicating a bromonium ion-mechanism for the ring closure. 6-endo-control of the alkenol cyclization thereby arises from the polar effect of the aryl substituent. Two methyl substituents bound to the alkene terminus are not similarly able to favor 6-endo-cyclization, because strain arising from methyl group repulsion, as the bromonium-activated π-bond and the hydroxyl oxygen approach, directs bromocyclization of tertiary prenyl-type substrates toward tetrahydrofuran formation. A hexasubstituted bromotetrahydropyran prepared from the oxidation/bromocyclization cascade served as starting material for synthesis of racemic aplysiapyranoid A, in a sequence of free radical and polar functional group interconversion.