Abstract
AbstractThe suitability of allenylphosphonates as substrates in phosphane‐catalyzed annulation reactions has been investigated. Despite their lower reactivity relative to allenyl esters, allenylphosphonates overall display the anticipated behavior: pyrrolines, tetrahydropyridines, and cyclopentenes bearing phosphoryl functions were obtained from imines, α,β‐unsaturated esters, and enones in Bu3P‐ or iBu3P‐promoted reactions. Enantioselective variants of these cyclization reactions afforded enantiomeric excesses of up to 90 % when phosphepine A2 was used as the chiral catalyst. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
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