Journal
CHEMICAL & PHARMACEUTICAL BULLETIN
Volume 53, Issue 4, Pages 355-360Publisher
PHARMACEUTICAL SOC JAPAN
DOI: 10.1248/cpb.53.355
Keywords
imino Wittig rearrangement; hydroximate; imidate; amino acid; oxime ether
Ask authors/readers for more resources
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-hydroxyphenylaianines, respectively, via the oxidative cleavage of a furan ring, ring-opening of oxazolidinone, and deprotection.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available