Synthesis of Novel Oxime Functionalized Aldol Products via Michael Addition of Oximes Onto Baylis–Hillman Adducts

Abstract Triphenylphosphine‐catalyzed Michael addition of oximes 2 onto Baylis–Hillman (B‐H) adducts 1 led to an easy access to a novel class of oxime functionalized aldol products 3. This demonstrates the first use of an oxygen‐centered nucleophile in Michael addition to B‐H adducts, without touching any other functional group. Deprotection of oxime in 3 was further demonstrated using molecular hydrogen (1 atm) and 10% Pd/C (cat.) to furnish functionalized 1,3‐diols 4 as potentially useful synthons with optional backbone choice (R3 and EWG). DRL Publication No. 354. Part of these results was presented at Pharmacophore 2004, January 16–17, 2004, an international symposium organized by Dr. Reddy's Laboratories Ltd. on the occasion of its achievement in drug discovery.