Reduction of a-benzyloxy acetylenic ketones with zinc borohydride afforded the erythro-acetylenic vicinal diols in 95% stereoselectivity, while reduction with K-selectride gave the isomeric threo-diols in 90% stereoselectivity. Repetition of 1,3-chiral transfer reaction by palladium catalyzed allyl
The stereoselective reduction of α-aminodeoxybenzoin derivatives with sodium borohydride
✍ Scribed by Benito Alcaide; Gerardo Escobar; JoséL. González-Simó; Carmen López-Mardomingo; Rafael Pérez-Ossorio; Joaquin Plumet
- Publisher
- Elsevier Science
- Year
- 1982
- Tongue
- French
- Weight
- 208 KB
- Volume
- 23
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Total stereoselectlvity IS observed In the sodium borohydride reduction of a-aminodeoxybenzoins and their hydrochlortdes In various hydroxyllc solvents RS-SR Isomer (erythro) was the only aminoalcohol obtained In a recent paper1 Kametani et al report the stereoselective reduction of a-aminopropiophenone derivatives with sodium borohydride The lower stereo-
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## Abstract The rates for the reduction of ketones with sodium borohydride are interpreted in terms of two parameters, both derived from force‐field calculations; __i.e.__ the strain difference between alcohol and ketone (Δ strain) and the steric hindrance towards approach of the hydride R. Models
Theor-oxoketene dithioacetals 1. are shown to undergo conjugate 1,4-reduction in highly regio-and chemoselective manner with sodium borohydride in acetic acid to afford the corresponding B-oxodithioacetals 5 in good yields. These results have been rationalized according to HSAB principle in terms of