ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
α-Silylated ketones (S)-2 (ee ≥ 98%), easily available through silylation or silylation/alkylation from ketones 1 using the (-)-(S)-1-amino-2-(methoxymethyl)pyrrolidine (SAMP)-/(+)-(R)-1-amino-2-(methoxymethyl)pyrrolidine (RAMP)-hydrazone method, are oxidized to give α-hydroxy-ketones (R)-5 of high enantiomeric purity (ee ≥ 98%) and in good overall yields (51-70%). The key step of the procedure is the silicon-directed diastereoselective oxidation of the corresponding silyl enol ethers of (S)-2, with m-chloroperbenzoic acid or 3-phenyl-2-(phenylsulfonyl)oxaziridine, followed by flash chromatography and desilylation.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19890720514
