Samarium dienolate mediated stereoselective synthesis of anti-1,3-diol monoesters via aldol-Tishchenko reaction

摘要

The reaction of an (E)-samarium dienolate, generated by the regioselective reductive cleavage of a plienylsulfonyl activated cyclopropyl ketone with samarium(II) iodide, with aliphatic and aromatic aldehydes gives the 2-substituted anti-1.3-diol monoester derivatives, stereo selectively, in good to excellent yields. The results represent the first report of a dienolate in the aldol-Tishchenko reaction and also provide an optically active pokol with (R)-glyceraldehyde. (c) 2006 Elsevier Ltd. All rights reserved.