Molecular Diversity

, Volume 9, Issue 4, pp 321–331

Polymer-supported and polymeric chiral guanidines: Preparation and application to the asymmetric Michael reaction of iminoacetate with methyl vinyl ketone

Full-length paper

DOI: 10.1007/s11030-005-8116-z

Cite this article as:
Wannaporn, D. & Ishikawa, T. Mol Divers (2005) 9: 321. doi:10.1007/s11030-005-8116-z

Summary

Polymer-supported and polymeric chiral guanidines carrying an imidazolidine skeleton are designed as polymer-based base catalysts. Thus, (R)-2-[(S)-1-hydroxymethyl-2-phenylethylimino]-4-phenylimidazolidine was newly prepared from (R)-phenylglycine as the key functional unit of these guanidines. Application of the polymer-based chiral guanidines to the asymmetric Michael reaction of t-butyl diphenyliminoacetate with MVK led to expected asymmetric induction in the Michael adduct with moderate enantioselectivity in the use of the latter polymeric chiral guanidines.

Key Words

asymmetric synthesiscatalystguanidineMichael reactionpolymerpreparation

Abbreviations

Boc

t-butoxycarbonyl

Cbz

carbobenzoxy

CDI

carbonyldiimidazole

DIEA

diisopropylethylamine

DMF

dimethylformamide

MVK

methyl vinyl ketone

PS

polystyrene

TFA

trifluoroacetic acid

THF

tetrahydrofuran

Copyright information

© Springer Science + Business Media, Inc. 2005

Authors and Affiliations

  1. 1.Graduate School of Pharmaceutical SciencesChiba UniversityChibaJapan