A General Stereocontrolled Synthesis of Opines through Asymmetric Pd‐Catalyzed N‐Allylation of Amino Acid Esters | Zendy

Albat Dominik | Zendy; Neudörfl JörgMartin | Zendy; Schmalz HansGünther | Zendy

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A General Stereocontrolled Synthesis of Opines through Asymmetric Pd‐Catalyzed N‐Allylation of Amino Acid Esters

Author(s) -

Albat Dominik,

Neudörfl JörgMartin,

Schmalz HansGünther

Publication year - 2021

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.202100259

Subject(s) - chemistry , allylic rearrangement , catalysis , palladium , ozonolysis , stereochemistry , cleavage (geology) , derivative (finance) , bond cleavage , oxidative cleavage , medicinal chemistry , organic chemistry , geotechnical engineering , fracture (geology) , financial economics , engineering , economics

A stereo‐divergent synthesis of natural and unnatural opines in stereochemically pure form is based on the direct palladium‐catalyzed N‐allylation of α‐amino acid esters (up to 97 % ee or 99 : 1 d.r.) using methyl (E)‐2‐penten‐4‐yl carbonate in the presence of only 1 mol% of a catalyst, prepared in‐situ from the C 2 ‐symmetric diphosphine i Pr‐MediPhos and [Pd(allyl)Cl] 2 . Selected target compounds (incl. a derivative of the drug enalapril) were efficiently obtained from the N‐allylated intermediates by oxidative cleavage (ozonolysis) of the allylic C=C bond under temporary N ‐Boc‐protection.

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