New convenient access to thioesters of alpha-amino acids from N,N-disubstitulted 2-aminoalk-2-enals

Authors
Rulev, AY Larina, LI Keiko, NA Voronkov, MG
Citation
Ay. Rulev et al., New convenient access to thioesters of alpha-amino acids from N,N-disubstitulted 2-aminoalk-2-enals, J CHEM S P1, (11), 1999, pp. 1567-1569
Citations number
32
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
11
Year of publication
1999
Pages
1567 - 1569
Database
ISI
SICI code
0300-922X(19990607):11<1567:NCATTO>2.0.ZU;2-X
Abstract
N,N-Disubstituted 2-aminoalk-2-enals 1 react with alkyl- or arylthiols to g ive unexpected thioesters of alpha-amino acid 3 in good yields. The same ty pe of product is formed when substrate 1b is treated with ethane-1,2-dithio l. The reaction proceeds via an intermediate 1,2-adduct which is transforme d, after a 1,3-shift, into the final thioester 3.