Synthesis of Methionine-Derived Endocyclic Sulfilimines and Sulfoximines

Hamid Marzag (1) , Marie Schuler (2) , Arnaud Tatibouët (2) , Vincent Reboul (1)

1 LCMT - Laboratoire de chimie moléculaire et thioorganique
2 ICOA - Institut de Chimie Organique et Analytique

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 tBuONa 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.

Mots clés: Amino acids; Asymmetric synthesis; Cyclization; Heterocycles; Sulfur

Domaines: Chimie organique

Hamid Marzag, Marie Schuler, Arnaud Tatibouët, Vincent Reboul. Synthesis of Methionine-Derived Endocyclic Sulfilimines and Sulfoximines. European Journal of Organic Chemistry, 2017, 2017 (4), pp.896 - 900. ⟨10.1002/ejoc.201601515⟩. ⟨hal-01830246⟩