ChemInform Abstract: WITTIG‐HORNER REACTION IN A HETEROGENEOUS MEDIUM. VI. SELECTIVITY OF THE REACTION ON BIFUNCTIONAL COMPOUNDS

Abstract

Zahlreiche Aldehyde (I) reagieren mit den funktionellen Phosphonsäureestern (II) zu den Olefinen (III).

Lithiated anions derived from (alkenyl)pentamethyl phosphoric triamides: Useful synthons for the stereoselective synthesis of 9-oxo- and 10-hydroxy-2(E)-decenoic acids, important components of queen substance and royal jelly of honeybee Apis mellifera

“…Although this strategy is limited by the instability of acrolein, the acrolein dialkylacetal approach raised the problem of competitive SN 2 0 allylic substitution [15]. An interesting solution is the copper catalyzed reaction to protected acrolein [16]. Most recent and effective syntheses of 7-oxo-octanal involve: a) preparation and reduction of 7-oxooctanoic acid to corresponding diol and oxidation with PCC [17]; b) preparation of 7,7-dimethoxy-heptanal followed by its methylenation, oxidation and deprotection [18] or c) the use of heptane-1,7-diol as substrate followed by its selective protection with THP group, and subsequent sequence oxidation, methylenation, oxidation and finally deprotection and again oxidation [19].…”