Communication
ChemComm
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by 3 Å MS, and then continued to undergo the chiral Fe(III)-
catalyzed enantiomer selective hydride transfer. Additionally,
glyoxal 4a could also coordinate to the chiral Fe(III) complex,
enabling the asymmetric addition of t-BuOH from the Re-face
to give (R)-5a. The perfect chiral environment created by the
N,N-dioxide–FeCl3 complex benefited both the dynamic kinetic
resolution and the enantioselective addition processes. Therefore,
excellent enantioselectivities were obtained regardless of the
reaction procedure.
In summary, we have developed a highly efficient FeCl3
complex of chiral N,N-dioxide for the asymmetric intra-
molecular Cannizzaro reaction, with advantages such as being
environmentally benign and air-insensitive. The reactions of
aryl and alkyl glyoxals with various alcohols gave the a-hydroxy
acid esters in high yields (up to 99%) and high enantioselec-
tivities (up to 97% ee). A mechanistic study revealed the perfect
enantioselective environment for the catalyst which accounts
for either the dynamic kinetic resolution process or the asym-
metric addition process. The outcomes accomplished using the
iron catalyst show the potential of earth-abundant iron for
asymmetric reactions.
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We appreciate financial support of the National Natural Science
Foundation of China (21432006, 21332003 and 21372162).
Notes and references
1 For recent reviews on iron catalysis, see: (a) A. Correa, O. G.
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