Conversion of isomeric 2:3 adducts (aminoacid–formaldehyde) to N-acyl-pseudoprolines derivatives

Autor:	André A. Pavia, Jacqueline Smadja, Jimmy Selambarom
Rok vydání:	2005
Předmět:	Serine chemistry.chemical_compound Chemistry Stereochemistry Organic Chemistry Drug Discovery Thiaproline Formaldehyde Threonine Biochemistry Tautomer Cysteine Adduct
Zdroj:	Tetrahedron Letters. 46:615-617
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2004.11.134
Popis:	Reaction of acyl chlorides or acid anhydrides with isomeric 2:3 adducts derived from condensation of l -serine ( 1a ), l -threonine ( 1b ) and l -cysteine ( 1c ) methyl esters with formaldehyde afforded N-acyl-pseudoprolines 7–19 in various yields. These 2:3 adducts can be considered as synthetic equivalents of oxaproline and thiaproline moieties. The present work revealed the versatile behaviour of the two 2:3 adducts as a consequence of the ring-chain tautomerism occurring in the five- and/or seven-membered rings.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f6a9b5e2ecb6d2db93a766f20d19c217 https://doi.org/10.1016/j.tetlet.2004.11.134 Zobrazit plný text záznamu Full Text from ScienceDirect