An intrumolecular hydride delivery process largely contributes during the double reduction of a-keto esters into diols by NaBH4. In the case of enolic a-keto esters, the first step of the process, the reduction of the keto group, oecured exclusively through an 1,2-hydride addition despite the predom
Diastereoselective NaBH4 Reductions of (dl) α-Keto Esters
✍ Scribed by B. Ben Hassine; M. Gorsane; J. Pecher; R. H. Martin
- Publisher
- Wiley (John Wiley & Sons)
- Year
- 2010
- Weight
- 283 KB
- Volume
- 94
- Category
- Article
- ISSN
- 0037-9646
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📜 SIMILAR VOLUMES
The reduction of a-keto esters derived from (IL)-1,2;5,6-biscyclohexylidene-3-terrbutyldimethysilyl-chiro -inositol with Selectride@ proceeded with high diastereoselectivity to afford the corresponding a-hydroxy esters. Addition of l&Crown-6 led to dramatic changeover in diastereofacial selectivity.
The stereoselective reduction of a-keto esters/a-keto amides, which have various chiral auxiliaries using SmI 2 , is examined. 2(S)-Methoxymethylpyrrolidine, 1,1,2(S)-and 1,1,2(R)-triphenylethanediol were found to be suitable chiral auxiliaries that produced the corresponding a-hydroxy ester and ami