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Synthesis of α‐Amino‐γ‐lactams through Pd‐Catalzed Intramolecular Allylic Alkylation of Sarcosine Allyl Amides
Author(s) -
Thies Sarah,
Kazmaier Uli
Publication year - 2014
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.201301659
Subject(s) - chemistry , sarcosine , tsuji–trost reaction , allylic rearrangement , intramolecular force , alkylation , medicinal chemistry , dichloromethane , palladium , amination , pyrrolidine , stereochemistry , glycine , catalysis , amino acid , organic chemistry , solvent , biochemistry
N ‐Protected amino acid allyl amides with an allylic leaving group can be used as substrates in palladium‐catalyzed allylic alkylation. Whereas intermolecular allylations proceed with excellent yields under standard conditions for enolate reactions, the intramolecular version is not a trivial issue. N ‐Protected glycine amides preferentially form piperidinones through N ‐allylation, but the corresponding sarcosine derivatives provide γ‐lactams in acceptable to good yields in dichloromethane, especially when the corresponding titanium enolates are formed.