Enantioselective Protonation in the Aza-Michael Reaction Using a Combination of Chiral Pd-µ-Hydroxo Complex with an Amine Salt

Abstract A highly enantioselective protonation of enolate intermediates in aza-Michael reaction was achieved by using the combination of a bifunctional chiral Pd-µ-hydroxo complex with aromatic amine salts. The reaction proceeded smoothly to give the desired β-amino carbonyl compounds bearing a ster...

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Published in:Synlett 2009-06, Vol.2009 (10), p.1631-1634
Main Authors: Hamashima, Yoshitaka, Tamura, Toshihiro, Suzuki, Shoko, Sodeoka, Mikiko
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creator Hamashima, Yoshitaka
Tamura, Toshihiro
Suzuki, Shoko
Sodeoka, Mikiko
description Abstract A highly enantioselective protonation of enolate intermediates in aza-Michael reaction was achieved by using the combination of a bifunctional chiral Pd-µ-hydroxo complex with aromatic amine salts. The reaction proceeded smoothly to give the desired β-amino carbonyl compounds bearing a stereogenic carbon center at the α-position in good yield with excellent enantioselectivity (up to 97% ee). Although reactions with salts of electron-deficient amines were slow, the introduction of free amine as an additive promoted the reaction to a synthetically useful level.
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title Enantioselective Protonation in the Aza-Michael Reaction Using a Combination of Chiral Pd-µ-Hydroxo Complex with an Amine Salt
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