Abstract
The scope and limitations of the diastereoselective 1,4-addition reaction of primary alcohols to γ-alkoxy-α,β-unsaturated esters were investigated. We found that a variety of sodium alkoxides, generated from the corresponding primary alcohols with NaH, underwent 1,4-addition reactions with (E)-enoates in CH 2Cl 2at -23 °C to give β-alkoxy esters in modest yields with good to excellent syn -selectivity, whereas stereoselectivity was not observed with the use of glycerol derivatives as nucleophiles. Cyclic acetal protection was found to play a pivotal role for the reaction to proceed.
Original language | English |
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Pages (from-to) | 161-174 |
Number of pages | 14 |
Journal | Synthesis (Germany) |
Volume | 53 |
Issue number | 1 |
DOIs | |
Publication status | Published - 2021 Jan 5 |
Externally published | Yes |
Keywords
- 1,4-addition
- cyclic acetals
- primary alcohols
- syn -selectivity
- γ-alkoxy-α,β-unsaturated esters
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry