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[3+2] Cycloaddition of trimethylenemethane (TMM) to α,β-unsaturated γ-lactam. Preparation of 5,5-fused proline surrogates by Edwin Jao; Stephane Bogen; Anil K Saksena; Viyyoor Girijavallabhan is a Chemistry article available to read on EtoBox.

What is [3+2] Cycloaddition of trimethylenemethane (TMM) to α,β-unsaturated γ-lactam. Preparation of 5,5-fused proline surrogates about?

Unsaturated lactam derived from (S)-pyroglutaminol undergoes a totally stereoselective cycloaddition reaction with (2-(acetoxymethyl)-3-allyl)trimethylsilane in the presence of Pd(P(OiPr) 3 ) 4 in refluxing toluene. This step was efficiently used to introduced the 5,5-fused framework desired for the preparation of novel proline surrogates.

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Author

Edwin Jao; Stephane Bogen; Anil K Saksena; Viyyoor Girijavallabhan

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4039)

Published

2003

Language

EN

Field

Chemistry (Physical Sciences)