78044-64-1Relevant academic research and scientific papers
ON THE STEREOSELECTIVITY OF THE α-ALKYLATION OF Β-HYDROXY ESTERS. ENANTIOSELECTIVE SYNTHESIS OF 4,4- AND 6,6-DISUBSTITUTED CYCLOHEX-2-EN-1-ONES.
Frater, Gyorgy
, p. 425 - 428 (1981)
Stereoselective α-alkylation of the optically active β-hydroxyester 1 gives rise to 2, which was converted to the 1,5-diketone 4.Regioselective aldolcondensation of the latter furnished (S)-5 and (S)-6 respectively, each with an e.e. of 86percent.
THE STEREOSELECTIVE α-ALKYLATION OF CHIRAL β-HYDROXY ESTERS AND SOME APPLICATIONS THEREOF
Frater, G.,Mueller, U.,Guenther, W.
, p. 1269 - 1278 (2007/10/02)
The stereoselectivity of the α-alkylation of chiral β-hydroxy ester is discussed.The configuration of the alkylated product was proved chemically (Scheme 2) .A one pot aldol-alkylation reaction was developed leading stereoselectively to racemic(S*,S*)-α-alkyl-β-hydroxy ester (Scheme 3,4) .Baker's yeast reduction of 2-alkyl-3-keto ester led to valuable chiral (2RS,3S)-intermediates, which were converted via the corresponding dianion to compounds with a chiral quaternary C atom (Scheme 6) .Synthetic applications of the above findings are shown in the synthesis of various chiral compounds (Scheme 8 and 9) .
