ethyl (3R)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate

Base Information

• Chemical Name: ethyl (3R)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate
• CAS No.: 1100114-72-4
• Molecular Formula: C₁₇H₂₅BO₄
• Molecular Weight: 304.194
• Mol file: 1100114-72-4.mol

Synonyms:ethyl (3R)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate

Chemical Property of ethyl (3R)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (3R)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate

There total 14 articles about ethyl (3R)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

ethyl (Z)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-acrylate (1593270-23-5) → ethyl (3R)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate (1100114-72-4)

Guidance literature:

With (+)-1,2-bis((2S,5S)-2,5-diphenylphospholanyl)ethane; hydrogen; nickel diacetate; at 80 ℃; for 48h; under 60804.1 Torr; Time; enantioselective reaction; Catalytic behavior; Autoclave;

DOI:10.1021/acs.orglett.9b00994

Reference yield: 91.0%

bis(pinacol)diborane (73183-34-3) + ethyl cinnamate (4192-77-2) → ethyl (3R)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate (1100114-72-4)

Guidance literature:

bis(pinacol)diborane; With (-)-ferrocenylmesitylimidazolium copper chloride; caesium carbonate; In toluene; for 0.166667h; Inert atmosphere; Glovebox; Sealed tube;

ethyl cinnamate; In methanol; toluene; at 0 ℃; for 1h; stereoselective reaction; Inert atmosphere;

DOI:10.1002/anie.201410118

Reference yield:

ethyl 3-phenyl-2-propenoate (103-36-6) + bis(pinacol)diborane (73183-34-3) → ethyl (3R)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate (1100114-72-4) + ethyl (3S)-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate (1006696-15-6)

Guidance literature:

With methanol; copper(I) bromide dimethylsulfide complex; (S)-5-isobutyl-2-mesityl-1-phenyl-5,6-dihydro-2H-imidazo[5,1-a]isoquinolin-4-ium chloride; potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 12h; enantioselective reaction; Inert atmosphere;

DOI:10.1039/c0cc02211j

upstream raw materials:

bis(pinacol)diborane

ethyl cinnamate

ethyl 3-phenyl-2-propenoate

benzenediazonium tetrafluoroborate