Synthesis of functionalized allenamides from ynamides by enolate Claisen rearrangement.

Org Lett

Laboratoire de Chimie Organique, ESPCI Paris Tech, CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France.

Published: April 2013

The Claisen rearrangement of N-Boc glycinates derived from ynamido-alcohols affords an efficient and stereoselective access to highly functionalized allenamides. These compounds undergo silver-catalyzed cyclization to 3-pyrrolines which are useful precursors for the synthesis of substituted pyrrolidines.

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http://dx.doi.org/10.1021/ol400402nDOI Listing

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