Synthesis of Methionine‐Derived Endocyclic Sulfilimines and Sulfoximines

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 necessar...

Full description

Saved in:
Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 2017; no. 4; pp. 896 - 900
Main Authors Marzag, Hamid, Schuler, Marie, Tatibouët, Arnaud, Reboul, Vincent
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 26.01.2017
Wiley Subscription Services, Inc
Wiley-VCH Verlag
Subjects
Amino acids
Asymmetric synthesis
Chemical Sciences
Chemistry
Chemistry, Organic
Cyclization
Heterocycles
Organic chemistry
Physical Sciences
Science & Technology
Sulfur
ORTHO-LITHIATION
DIRECTING GROUP
OXIDATION
BENZOTHIAZINES
Heterocycles
ASYMMETRIC-SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
Amino acids
C-H ACTIVATION
ALKYLIDENE TRANSFER REAGENTS
Asymmetric synthesis
Cyclization
RING-CLOSING METATHESIS
SULFONIMIDOYL CARBANIONS
Sulfur
Online AccessGet full text

Cover

More Information
Summary: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. A one‐pot, two‐step asymmetric synthesis of endocyclic methionine sulfilimines and sulfoximines from methionine derivatives is reported.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201601515