Spirobicyclic Diamines 2: Synthesis of Homochiral Diastereoisomeric Proline Derived [4,4]-Spirolactams

Authors

Fintan Kelleher, Technological University DublinFollow
Sinead Kelly, Technological University Dublin

Document Type

Article

Rights

Available under a Creative Commons Attribution Non-Commercial Share Alike 4.0 International Licence

Disciplines

Organic Chemistry

Publication Details

Tetrahedron Letters (v.47, #30; pp.5247-5250)

Abstract

L-Proline derived diastereoisomeric [4.4]-spirolactams have been prepared by a reductive-amination reaction of (R)- or (S)-alanine methyl ester followed by thermal cyclisation of the resulting amine onto the proline ester group in refluxing toluene. Under similar conditions (R)- or (S)-phenylalanine methyl ester gave no cyclisation products, while R- or S-a-methylbenzylamine required treatment with NaNH₂ in refluxing toluene to induce cyclisation giving diastereoisomeric [4.4]-spirolactams

Recommended Citation

Kelleher, F. and Kelly, S. Spirobicyclic diamines 2: Synthesis of homochiral diastereoisomeric proline derived [4,4]-spirolactams. Tetrahedron Letters (v.47, #30; pp.5247-5250)

Funder

Irish Government