(2E,4R)-4-(4’,4’,5’,5’-tetramethyl-1’,3’,2’-dioxaborolanyl)-6-phenylhex-2-ene

Base Information

Chemical Name:(2E,4R)-4-(4’,4’,5’,5’-tetramethyl-1’,3’,2’-dioxaborolanyl)-6-phenylhex-2-ene
CAS No.:1428538-05-9
Molecular Formula:C₁₈H₂₇BO₂
Molecular Weight:286.222
Hs Code.:

Synonyms:(2E,4R)-4-(4’,4’,5’,5’-tetramethyl-1’,3’,2’-dioxaborolanyl)-6-phenylhex-2-ene

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Chemical Property of (2E,4R)-4-(4’,4’,5’,5’-tetramethyl-1’,3’,2’-dioxaborolanyl)-6-phenylhex-2-ene

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Technology Process of (2E,4R)-4-(4’,4’,5’,5’-tetramethyl-1’,3’,2’-dioxaborolanyl)-6-phenylhex-2-ene

There total 5 articles about (2E,4R)-4-(4’,4’,5’,5’-tetramethyl-1’,3’,2’-dioxaborolanyl)-6-phenylhex-2-ene 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: 77.0%

: 673-31-4
phenprobamate

: 83947-58-4
4,4,5,5-tetramethyl-2-[(1E)-prop-1-en-1-yl]-1,3,2-dioxaborolane

: 1428538-05-9
(2E,4R)-4-(4’,4’,5’,5’-tetramethyl-1’,3’,2’-dioxaborolanyl)-6-phenylhex-2-ene

Guidance literature:: phenprobamate; With (2-methylpropyl)lithium; In diethyl ether; hexane; cyclohexane; at -78 ℃; for 5h;

4,4,5,5-tetramethyl-2-[(1E)-prop-1-en-1-yl]-1,3,2-dioxaborolane; In diethyl ether; hexane; cyclohexane; at -78 ℃; for 1h;

With magnesium dibromide etherate; In diethyl ether; hexane; cyclohexane; at 20 ℃; for 16h; enantioselective reaction; Reflux;
DOI:10.1021/ja401564z

Reference yield: 70.0%

: 218601-55-9
3-phenylpropyl N,N-diisopropylcarbamate

: 83947-58-4
4,4,5,5-tetramethyl-2-[(1E)-prop-1-en-1-yl]-1,3,2-dioxaborolane

: 1428538-05-9
(2E,4R)-4-(4’,4’,5’,5’-tetramethyl-1’,3’,2’-dioxaborolanyl)-6-phenylhex-2-ene

Guidance literature:: 3-phenylpropyl N,N-diisopropylcarbamate; With sec.-butyllithium; (-)-l-sparteine; In diethyl ether; at -78 ℃; for 5h;

4,4,5,5-tetramethyl-2-[(1E)-prop-1-en-1-yl]-1,3,2-dioxaborolane; In diethyl ether; at -78 ℃; for 1h;

With magnesium bromide; In diethyl ether; at 20 ℃; for 16h; Reflux;
DOI:10.1002/chem.201303683

Reference yield:

: 130700-03-7
(3Z)-6-phenylhex-3-en-2-ol

: 1428538-05-9
(2E,4R)-4-(4’,4’,5’,5’-tetramethyl-1’,3’,2’-dioxaborolanyl)-6-phenylhex-2-ene

: (S,E)-4,4,5,5-tetramethyl-2-(1-phenylhex-4-en-3-yl)-1,3,2-dioxaborolane

Guidance literature:: Multi-step reaction with 2 steps

1.1: pyridine / dichloromethane / 17 h / 0 - 20 °C / Inert atmosphere

2.1: tetrakis(acetonitrile)copper(I)tetrafluoroborate; C₂₄H₄₄N₂P₂Si₂; potassium tert-butylate / tetrahydrofuran / 0.25 h / Inert atmosphere; Glovebox; Sealed tube

2.2: 24 h / -40 °C / Inert atmosphere; Sealed tube

With pyridine; tetrakis(acetonitrile)copper(I)tetrafluoroborate; potassium tert-butylate; C₂₄H₄₄N₂P₂Si₂; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jacs.0c08899