Download PDF
Synfacts 2006(9): 0955-0955  
DOI: 10.1055/s-2006-949231
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Amine/Protonic Acid Catalyzed Michael Addition

Contributor(s): Benjamin List, Sonja Mayer
S. V. Pansare*, K. Pandya
Memorial University of Newfoundland, Canada
Further Information

Publication History

Publication Date:
23 August 2006 (online)

    Permissions and Reprints

Significance

Di- and triamine pyrrolidine derivatives 1 and 2 were synthesized from Boc-protected S-proline in three steps, and their p-TsOH salts used as catalysts for the Michael reaction of cyclo­hexanone 3 with several nitroalkenes 4. Michael products 5 could be obtained with good diaste­reoselection (from 5:1 to 20:1) and excellent enantiomeric ratios (up to >99:1). So far cyclopentanone did not give high yields and selectivities. Plausible transition states are shown, also explaining the steric role of the used acid additives.