Synthesis of Chiral α‐Fluoroketones through Catalytic Enantioselective Decarboxylation | Zendy

Nakamura Masaharu | Zendy; Hajra Alakananda | Zendy; Endo Kohei | Zendy; Nakamura Eiichi | Zendy

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Synthesis of Chiral α‐Fluoroketones through Catalytic Enantioselective Decarboxylation

Author(s) -

Nakamura Masaharu,

Hajra Alakananda,

Endo Kohei,

Nakamura Eiichi

Publication year - 2005

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200502703

Subject(s) - enantioselective synthesis , stereocenter , chemistry , decarboxylation , racemization , chirality (physics) , substituent , palladium , total synthesis , asymmetric carbon , ligand (biochemistry) , stereochemistry , combinatorial chemistry , chiral ligand , kinetic resolution , catalysis , organic chemistry , optically active , biochemistry , nambu–jona lasinio model , chiral symmetry breaking , physics , receptor , quantum mechanics , quark

A conceptually new approach affords optically active α‐fluoroketones 3 in high yields with up to 99 % ee from racemic α‐fluoro‐β‐ketoesters 1 in the presence of a chiral phosphinooxazoline ligand 2 . The palladium‐catalyzed decarboxylation/allylation reaction also allows the highly enantioselective construction of an all‐carbon quaternary center. dba=dibenzylideneacetone.

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