SYNTHETIC STUDIES ON alpha,alpha-DISUBSTITUTED AMINO ACIDS EMPLOYING (2S, 4R)-4-HYDROXYPROLINE AS THE CHIRAL POOL: PREPARATION OF METHYL O-BENZYL-2-(alpha-CYANOMETHYL)-D-TYROSINATE AND DIMETHYL 2-(4-HYDROXYBENZYL)-L- ASPARTATE

Methyl O-benzyl-2-(alpha-cyanomethyl)-D-tyrosinate and dimethyl 2-(4-hydroxybenzyl)-L-aspartate were synthesized starting from (2S,4R)-4-hydroxyproline via Beckmann fragmentation of the corresponding oxime tosylate.

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Bibliographic Details
Published inHeterocycles Vol. 86; no. 1; pp. 659 - 668
Main Authors Nagahara, Ryohei, Hisa, Chihiro, Kojima, Noriko, Yamamoto, Naoshi, Honda, Toshio
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 2012
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Beckmann Fragmentation
DIASTEREOSELECTIVITY
(2S,4R)-4-Hydroxyproline
INTERMEDIATE
DERIVATIVES
2-Benzylaspartate
Oxime Tosylate
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Summary:Methyl O-benzyl-2-(alpha-cyanomethyl)-D-tyrosinate and dimethyl 2-(4-hydroxybenzyl)-L-aspartate were synthesized starting from (2S,4R)-4-hydroxyproline via Beckmann fragmentation of the corresponding oxime tosylate.
ISSN:0385-5414
1881-0942
DOI:10.3987/COM-12-S(N)9