Stereoselective synthesis of beta-hydroxyphenylalanines using imino 1,2-Wittig rearrangement of hydroximates.
The imino 1,2-Wittig rearrangement of hydroximates containing a furan ring provides a novel method for the synthesis of beta-hydroxy-alpha-amino acids. Upon treatment with LDA, hydroximates smoothly underwent the rearrangement to give Z-2-hydroxyoxime ethers in good yield, which were converted into both cis- and trans-oxazolidinones with high stereoselectivity. The cis- and trans-oxazolidinones were stereoselectively converted into erythro- and threo-beta-hydroxyphenylalanines, respectively, via the oxidative cleavage of a furan ring, ring-opening of oxazolidinone, and deprotection.
Miyata
Okiko
O
Kobe Pharmaceutical University, Kobe.
Asai
Hiroshi
H
Naito
Takeaki
T
D000215:Acylation; D007202:Indicators and Reagents; D010084:Oxidation-Reduction; D010091:Oximes / Q000138:chemical synthesis*; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D013237:Stereoisomerism
D007202:Indicators and Reagents; D010091:Oximes; C013048:beta-hydroxyphenylalanine; D010649:Phenylalanine