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Chemoselectivity in the reduction of aldehydes and ketones with amine boranes

✍ Scribed by Glenn C. Andrews

Publisher
Elsevier Science
Year
1980
Tongue
French
Weight
200 KB
Volume
21
Category
Article
ISSN
0040-4039

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✦ Synopsis

Ammonia borane and primary amine boranes are highly chemoselective reducing agents for aldehydes and ketones. There has been much recent interest in the development of chemoselective1s2 reducing agents capable of distinguishing aldehyde and ketone functionality in a predictable manner. 'a-si While all of these reagents are capable of reducing an aldehyde in the presence of a methyl ketone, few3a,3d.3e,sg,3i have the ability to distinguish between an aldehyde and a more reactive ketone such as cyclohexanone. Of those capable of such discrimination all have serious drawbacks: limited availability and high cost (g-borabicyclo[3.3.l]nonane-pyridine complex,3' di-n-butylg-borabicyclo[3.3.l]nonane "ate" complex, 3a), the need for the use of excess reagent, quenching

πŸ“œ SIMILAR VOLUMES

The synthetic utility of amine borane re
The synthetic utility of amine borane reagents in the reduction of aldehydes and ketones
✍ G.C. Andrews; T.C. Crawford πŸ“‚ Article πŸ“… 1980 πŸ› Elsevier Science 🌐 French βš– 223 KB

Primary and secondary amine boranes have been shown to be mild, efficient, and stereoselective reducing agents for aldehydes and ketones in protic or non-protic solvents with reactivity patterns different than diborane or sodium borohydride. During the course of our studies on new stereo-and them,-s