A Solid-Supported Stereoselective Multicomponent Reaction

G. Byk; E. Kabha

doi:10.1055/s-2006-941902

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Synfacts 2006(7): 0739-0739
DOI: 10.1055/s-2006-941902

Polymer-Supported Synthesis

A Solid-Supported Stereoselective Multicomponent Reaction

Contributor(s): Yasuhiro Uozumi, Maki Minakawa
G. Byk*, E. Kabha
Bar Ilan University, Ramat-Gan, Israel

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Publikationsdatum:
22. Juni 2006 (online)

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Significance

A solid-supported stereoselective multicomponent reaction is described. Polymer-supported β -keto- γ-lactam 2 was prepared in three steps starting from the p-nitrophenyl carbamate Wang resin 1. Treatment of 2 with two equivalents of benzaldehyde and one equivalent of urea in acetic acid at 60 °C led to a new spiro-bicyclic β-keto- γ -lactam scaffold 3 (single diastereomer). Three chiral carbons (one pseudochiral) were generated in one pot in 28% overall yield for five steps.