(-)-α-pinene
L-diisopinocampheylborane
Conditions | Yield |
---|---|
With borane N-ethyl-N-isopropylaniline complex In 1,4-dioxane hydroboration; | 99% |
With dimethylsulfide borane complex In tetrahydrofuran at 20℃; Inert atmosphere; | 73% |
With sodium tetrahydroborate; boron trifluoride diethyl etherate |
(-)-α-pinene
dimethylsulfide borane complex
L-diisopinocampheylborane
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 16h; Inert atmosphere; | 82% |
In tetrahydrofuran at 0℃; for 0.5h; | 60% |
In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; | 52% |
In tetrahydrofuran | |
In tetrahydrofuran at 0℃; |
dimethylsulfide borane complex
(1R,5R)-(+)-β-pinene
L-diisopinocampheylborane
Conditions | Yield |
---|---|
In tetrahydrofuran pinene was slowly added to THF soln. of BMS at 0°C (N2); stirring for 2.5 h; evapn.; |
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; stereoselective reaction; |
1-benzyl-3-methyl-1H-imidazol-3-ium iodide
L-diisopinocampheylborane
Conditions | Yield |
---|---|
With potassium hexamethylsilazane In tetrahydrofuran at 25℃; Inert atmosphere; Schlenk technique; | 83% |
benzaldehyde
L-diisopinocampheylborane
3-phenyl-1-(tributylstannyl)-1,2-propadiene
Conditions | Yield |
---|---|
In diethyl ether Sn compd. in Et2O treated with B compd. at 0°C for 5 h, C6H5CHO added at -78°C, stirred at -78°C for 8 h; NaHCO3 and H2O2 added at 0°C; 94 % ee; | 76% |
3-phenyl-propionaldehyde
L-diisopinocampheylborane
3-phenyl-1-(tributylstannyl)-1,2-propadiene
Conditions | Yield |
---|---|
In diethyl ether Sn compd. in Et2O treated with B compd. at 0°C for 5 h, C6H5(CH2)2CHO added at -78°C, stirred at -78°C for 8 h; NaHCO3 and H2O2 added at 0°C; 94 % ee; | 71% |
L-diisopinocampheylborane
Conditions | Yield |
---|---|
With potassium hexamethylsilazane In tetrahydrofuran at 25℃; Inert atmosphere; Schlenk technique; | 60% |
N-methyl-N'-phenyl imidazolium iodide
L-diisopinocampheylborane
Conditions | Yield |
---|---|
With potassium hexamethylsilazane In tetrahydrofuran at 25℃; Inert atmosphere; Schlenk technique; | 56% |
1,3-dimethylimidazolim iodide
L-diisopinocampheylborane
Conditions | Yield |
---|---|
With potassium hexamethylsilazane In tetrahydrofuran at 20℃; for 20h; Sealed tube; Inert atmosphere; Glovebox; | 37% |
With potassium hexamethylsilazane In tetrahydrofuran at 25℃; for 20h; Inert atmosphere; Schlenk technique; | 37% |
L-diisopinocampheylborane
Conditions | Yield |
---|---|
With potassium hexamethylsilazane In tetrahydrofuran at 20℃; for 20h; Sealed tube; Inert atmosphere; Glovebox; | 34% |
L-diisopinocampheylborane
Conditions | Yield |
---|---|
With potassium hexamethylsilazane In tetrahydrofuran at 25℃; Inert atmosphere; Schlenk technique; | 34% |
Conditions | Yield |
---|---|
With Pinene In tetrahydrofuran at -25℃; for 30h; asymmetric hydroboration; Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With Pinene In tetrahydrofuran at -25℃; for 76h; asymmetric hydroboration; Title compound not separated from byproducts; |
1-ethoxycyclopentene
L-diisopinocampheylborane
Conditions | Yield |
---|---|
With Pinene In tetrahydrofuran at -25℃; for 80h; asymmetric hydroboration; Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With Pinene In tetrahydrofuran at -15℃; for 120h; asymmetric hydroboration; Title compound not separated from byproducts; |
L-diisopinocampheylborane
Conditions | Yield |
---|---|
With Pinene In tetrahydrofuran at -10℃; for 72h; asymmetric hydroboration; Title compound not separated from byproducts; |
L-diisopinocampheylborane
2-allenyl-4,4,5,5-tetraphenyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
In dichloromethane at 0℃; for 2.5h; | |
In dichloromethane at 0 - 23℃; |
L-diisopinocampheylborane
2-allenyl-[1,3,2]-dioxaborinane
Conditions | Yield |
---|---|
In dichloromethane at 0 - 20℃; |
L-diisopinocampheylborane
2-allenyl-4,4,5,5-tetraphenyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
In dichloromethane at 0℃; for 2h; |
Conditions | Yield |
---|---|
In diethyl ether at 0℃; for 2h; | |
In tetrahydrofuran at 20℃; for 4h; Inert atmosphere; |
(R)-1-methoxy-4-((pent-4-yn-2-yloxy)methyl)benzene
L-diisopinocampheylborane
Conditions | Yield |
---|---|
In tetrahydrofuran at -35 - 20℃; for 2.5h; |
L-diisopinocampheylborane
B-allyldiisopinocampheylborane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diethyl ether / 2 h / 0 °C 2: diethyl ether / 1 h / 20 °C View Scheme |
L-diisopinocampheylborane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: CH2Cl2 / 2 h / 0 °C 2: CH2Cl2 / 18 h / -78 °C View Scheme |
L-diisopinocampheylborane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: CH2Cl2 / 2 h / 0 °C 2: CH2Cl2 / 2.5 h / -78 °C View Scheme |
Conditions | Yield |
---|---|
Norbornene is hydroborated with Ipc2BH at -25°C (83% ee).; |
L-diisopinocampheylborane
B-bromodiisopinocampheylborane
Conditions | Yield |
---|---|
With hydrogen bromide In pentane 0°C;; |
L-diisopinocampheylborane
B-iododiisopinocampheylborane
Conditions | Yield |
---|---|
With iodine In pentane 0°C;; |
L-diisopinocampheylborane
B-chlorodiisopinocampheylborane
Conditions | Yield |
---|---|
With hydrogenchloride In pentane 0°C;; |
Conditions | Yield |
---|---|
With sodium hydroxide; acetaldehyde In tetrahydrofuran mixt. of B compd. and pinene was kept at 0°C (N2) for 3 d; cooling to -25°C, addn. of cis-butene; stirring for 6 h; treatment with AcH with stirring at 25°C for 36 h, evapn., addn. of pentane, treatment with aq. NaOH; treatment with aq. HCl, extn. with Et2O, drying in vac.; |
Molecular Structure of Diisopinocampheylborane (CAS No.21947-87-5):
Molecular Formula: C20H35B
Molecular Weight: 286.30
CAS No: 21947-87-5
IUPAC Name: bis {(1S,2S,3S,5R)-2,6,6-Trimethylbicyclo [3.1.1] heptan-3-yl} borane
Diisopinocampheylborane was reported in 1961 by Zweifel and Brown in a pioneering demonstration of asymmetric synthesis using boranes.
Diisopinocampheylborane (CAS No.21947-87-5) is mainly used for the synthesis of chiral secondary alcohols.
Diisopinocampheylborane is now more commonly generated from borane-methyl sulfide (BMS).
Diisopinocampheylborane (CAS No.21947-87-5), its synonyms are (+)-Diisopinocampheylborane ; Bis[(1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]borane .
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View