|
Function |
Transformation |
Type |
Caveat |
Reference |
|
|
Reagent |
Asymmetric synthesis |
Reduction |
Mild, chemoselective reducing agent for the carbonyl function, but essentially inert to other functional groups e.g. epoxides, esters, lactones, carboxylic acid salts, nitriles and nitro groups. |
JOC 1987, 52, 5406 |
|
Reagent |
Organometallic Chemistry |
Hydrometallation |
Catalyzes [2+2] cycloadditions. |
|
|
Reagent |
Reduction |
Aldehyde to alcohol |
In aprotic solvents such as dioxane. |
FF 1967, I, 584 |
|
Reagent |
Reduction |
Alkyl halide to alkane |
FeCl3 in ether converts epoxides to chlorohydrins. |
JOC 1982, 47, 276 |
|
Reagent |
Reduction |
Amide to aldehyde |
Deprotection of a silyl ether. |
TL 1981, 22, 3815 |
|
Reagent |
Reduction |
Amide to amine |
?,?-Unsaturated ketones are reduced to allylic alcohols. |
|
|
Reagent |
Reduction |
Anhydride to alcohol |
LaCl3 has been used for acetalization and thioacetalization of aldehydes and ketones. |
|
|
Reagent |
Reduction |
Carboxylic acid to alcohol |
Amines can be formed from the reduction of azides and hydrazines. |
|
|
Reagent |
Reduction |
Carboxylic ester to alcohol |
Reductive amination between a ketone and an amine gives a good yield of dialkylamine. |
|
|
Reagent |
Reduction |
Epoxide to alcohol |
|
COS 1991, 8, Chapters 1.1-4.8 |
|
Reagent |
Reduction |
Ketone to alcohol |
Oxazoles are reduced to amides and piderines are reduced to piperidines. |
|
|
Reagent |
Reduction |
Nitrile to amine |
A dilute solution of CPA in isopropanol is used as the catalyst for Hydrosilylation of alkenes and alkynes to give alkylsilanes and alkenylsilanes. Hydrosilylation followed by hydrogen peroxide oxidation provides alcohols (from alkenes) and ketones (from |
|
|
Reagent |
Reduction |
Nitro to amine |
Will do hetero-Diels-Alder reactions via intermediate diacylimines. |
|
|
Reagent |
Reduction |
Tosylate to alkane |
Vinylic sulfones are reduced to the corresponding alkenes with retention of configuration. |
TL 1978, 1657 |