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Catalytic Enantioselective Protonation of α‐Oxygenated Ester Enolates Prepared through Phospha‐Brook Rearrangement
Author(s) -
Hayashi Masashi,
Nakamura Shuichi
Publication year - 2011
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.201007568
Subject(s) - enantioselective synthesis , protonation , catalysis , chemistry , enantiomer , cinchona , organic chemistry , medicinal chemistry , cinchona alkaloids , ion
Phosphonates go chiral : The organocatalytic enantioselective reaction of α‐ketoesters with phosphites using cinchona alkaloids and Na 2 CO 3 has afforded α‐phosphonyloxy esters with high enantioselectivities (see scheme). This process allows the formation of both enantiomers of the product. A catalyst loading of as low as 2 mol % does not result in a significant decrease of the enantioselectivity.