856908-45-7Relevant articles and documents
Stereoselective synthesis of β-hydroxyphenylalanines using imino 1,2-Wittig rearrangement of hydroximates
Miyata, Okiko,Asai, Hiroshi,Naito, Takeaki
, p. 355 - 360 (2007/10/03)
The imino 1,2-Wittig rearrangement of hydroximates containing a furan ring provides a novel method for the synthesis of β-hydroxy-α-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 thereo-β-hydroxypheny lalanines, respectively, via the oxidative cleavage of a furan ring, ring-opening of oxazolidinone, and deprotection.