Abstract
An efficient synthesis of chiral syn-α,γ-dihydroxycarbonyl units from readily available achiral precursors in three pots under mild conditions was developed. This method explored the asymmetric direct cross-aldol reaction of two different aldehydes in the presence of an organocatalyst to generate a chiral βhydroxyaldehyde, which was converted into a 4-nitromethyl-1,3-dioxane derivative as a diastereo-mixture via a sequence of nitroalkane addition and acetalization. The 4-nitromethyl-1,3-dioxane derivative was then transformed either to a carboxylic ester or to an aldehyde/ketone. The chiral syn-α,γ-dialkoxy esters and aldehydes/ketones were all obtained with excellent enantiopurity and diastereoselectivity after a base-promoted epimerization.
Original language | English |
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Pages (from-to) | 940-943 |
Number of pages | 4 |
Journal | Chemistry Letters |
Volume | 49 |
Issue number | 8 |
DOIs | |
Publication status | Published - 2020 Aug 5 |
Keywords
- Asymmetric aldol reaction
- Organocatalysis
- Pot economy
ASJC Scopus subject areas
- Chemistry(all)