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Synfacts 2007(8): 0801-0801  
DOI: 10.1055/s-2007-968794
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Asymmetric, exo-Selective Synthesis of trans-4,5-Disubstituted Pyrrolidines

Contributor(s): Victor Snieckus, Katie Groom
P. Garner*, J. Hu, C. G. Parker, W. J. Youngs, D. Medvetz
Case Western Reserve University, Cleveland and University of Akron, USA
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Publication History

Publication Date:
24 July 2007 (online)

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Significance

Reported is a Cu(I)-catalyzed, exo-selective [C+CN+CC] three-component coupling among an enolizable aldehyde, an azomethine ylide (bearing Oppolzer’s chiral camphorsultam to induce the asymmetric 1,3-dipolar cycloaddition) and a mono- or disubstituted electron-deficient dipolarophile. Numerous highly functionalized trans-4,5-disubstituted pyrrolidines have been produced with high levels of diastereoinduction, resulting from the kinetic diastereofacial selectivity established by the camphorsultam auxiliary. Both enolizable and α-chiral aldehydes were effectively employed in this reaction, which simultaneously and efficiently generates two new C-C bonds and four stereocenters.