Premium
Synthesis of Methionine‐Derived Endocyclic Sulfilimines and Sulfoximines
Author(s) -
Marzag Hamid,
Schuler Marie,
Tatibouët Arnaud,
Reboul Vincent
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601515
Subject(s) - methionine , chemistry , yield (engineering) , deprotonation , organic chemistry , amino acid , biochemistry , thermodynamics , ion , physics
The asymmetric synthesis of endocyclic methionine sulfilimines and sulfoximines from methionine derivatives was explored. The cyclization was performed by using phenyliodine diacetate (PIDA). In the case of l ‐methionine, dehydromethionine was obtained, and a deprotonation step by t BuONa was necessary to yield the corresponding sulfilimine. On the other hand, the cyclic sulfilimine of methionine methyl ester, methylthiopropylamine, and l ‐methioninol were synthesized in a single step by using PIDA. Owing to their instability, the sulfilimines were oxidized to their corresponding sulfoximines in good yields.