The stereoselective α-alkylation of chiral β-hydroxy esters and some applications thereof |
| |
Authors: | G Fráter U Müller W Günther |
| |
Institution: | Givaudan Research Company Ltd., CH-8600 Duebendorf, Switzerland |
| |
Abstract: | 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). |
| |
Keywords: | |
本文献已被 ScienceDirect 等数据库收录! |
|