The first chiral phosphine-catalyzed activation of acrylates for intramolecular formal [2 + 4] reactions with unsaturated imines is described. The catalytic reactions afford N-heterocycles with exceptionally high diastereo- and enantioselectivities. The [2 + 4] products are amenable for further transformations to useful molecules such as chiral piperidines and multicyclic structures. © 2012 American Chemical Society.

Rakesh Ganguly

SNU Management

Z. Jin

R. Yang

Y. Du

B. Tiwari

Y.R. Chi

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Shiv Nadar University

Organic Letters

Enantioselective intramolecular formal [2 + 4] annulation of acrylates and α,β-unsaturated imines catalyzed by amino acid derived phosphines