2-[(1S,2S)-1-(dimethylphenylsilyl)cyclopropan-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-[(1S,2S)-1-(dimethylphenylsilyl)cyclopropan-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 1070797-03-3
• Molecular Formula: C₁₇H₂₇BO₂Si
• Molecular Weight: 302.297
• Mol file: 1070797-03-3.mol

Synonyms:2-[(1S,2S)-1-(dimethylphenylsilyl)cyclopropan-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of 2-[(1S,2S)-1-(dimethylphenylsilyl)cyclopropan-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

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Technology Process of 2-[(1S,2S)-1-(dimethylphenylsilyl)cyclopropan-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 2 articles about 2-[(1S,2S)-1-(dimethylphenylsilyl)cyclopropan-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 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: 86.0%

(Z)-3-(dimethylphenylsilyl)-2-propen-1-yl methyl carbonate (1083213-14-2) + bis(pinacol)diborane (73183-34-3) → 2-[(1S,2S)-1-(dimethylphenylsilyl)cyclopropan-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1070797-03-3) + dimethyl(phenyl)(1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl)silane (401513-48-2)

Guidance literature:

With copper (I) tert-butoxide; (R)-segphos; In tetrahydrofuran; at 30 ℃; for 7h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1002/anie.200802342

Reference yield: 4.0%

(Z)-3-(dimethylphenylsilyl)-2-propen-1-yl methyl carbonate (1083213-14-2) + bis(pinacol)diborane (73183-34-3) → 2-[(1S,2S)-1-(dimethylphenylsilyl)cyclopropan-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1070797-03-3) + cis-1-(dimethylphenylsilyl)cyclopropan-2-yl(pinacolato)boronate + dimethyl(phenyl)(1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl)silane (401513-48-2)

Guidance literature:

With catalyst:Cu(OtBu)/(R,R)-quinoxP*; In tetrahydrofuran; react. of (Z)-(CH3)3Si(CH)2CH2OCO2CH3 and (BO2C2(CH3)4)2 (2 equiv.) at 30 degree.C for 8 h in presence of Cu(OtBu)/(R,R)-qinoxP catalyst; yield of trans-(1S,2S)-1-(Me2PhSi)C3H4-2-(B(pin)) is 91% in 91% ee;

DOI:10.1002/anie.200802342

upstream raw materials:

(Z)-3-(dimethylphenylsilyl)-2-propen-1-yl methyl carbonate

bis(pinacol)diborane