Highly diastereoselective mannich-type reactions of chiral N-acylhydrazones

The Journal of Organic Chemistry
Mikkel F JacobsenTroels Skrydstrup

Abstract

The Lewis acid-mediated addition of silyl enolates to easily accessible homochiral N-acylhydrazones derived from 3-amino-2-oxazolidinones proceeded in yields up to 71% and diastereomeric ratios of 99:1. In most cases, optimal reaction conditions entailed the simple use of ZnCl(2) in acetonitrile at room temperature. Hydrazones derived from phenyl-, isopropyl-, and benzyl-substituted 2-oxazolidinones were examined in the reaction in terms of yield and diastereoselectivity. The facile SmI(2)-mediated N-N bond cleavage of the formed hydrazines was demonstrated yielding a beta-amino acid derivative. Hence, the overall reaction sequence constitutes an efficient asymmetric Mannich-type reaction. The sense of diastereoselectivity was explained by a preferential attack on the less shielded Si face of the chiral hydrazones and confirmed by means of X-ray crystallography.

References

Oct 5, 2001·Journal of the American Chemical Society·G K Friestad, J Qin
May 16, 2002·Journal of the American Chemical Society·Shū KobayashiKei Manabe
Aug 30, 2003·The Journal of Organic Chemistry·Mikkel F Jacobsen, Troels Skrydstrup
Nov 5, 2003·Angewandte Chemie·Gregory K FriestadErik L Ruggles

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Citations

Aug 2, 2005·Angewandte Chemie·Masaharu Sugiura, Shū Kobayashi
Aug 26, 2016·Beilstein Journal of Organic Chemistry·Motoyuki IsodaAkira Ando
Aug 26, 2009·The Journal of Organic Chemistry·Debasis SamantaGregory R Cook
Mar 9, 2011·The Journal of Organic Chemistry·Filip ColpaertNorbert De Kimpe
Apr 14, 2005·Journal of the American Chemical Society·Amelia A FullerAnna K Mapp
Jan 18, 2008·Journal of the American Chemical Society·Ryosuke MatsubaraShū Kobayashi

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