Diastereoselective reduction of α-keto esters derived from functionalised cholic acid
✍ Scribed by Uday Maitra; Packiarajan Mathivanan
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- English
- Weight
- 233 KB
- Volume
- 5
- Category
- Article
- ISSN
- 0957-4166
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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
Highly diastereoselective aldol additions of (2R,4S)-3-tert-butyl 4-methyl 2-tert-butyloxazolidine-3,4-dicarboxylate (1) are reported. The utility of the highly substituted oxazolidines of type 1 for diastereoselective a-addition of the fully protected amino acid L-serine with achiral and chiral car
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