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.

Keywords:

• Aldol products
• Baylis–Hillman adducts
• deprotection of oximes
• 1,3‐diols
• Michael addition
• oximes
• triphenylphosphine

Acknowledgments

We are thankful to the management of Discovery Research, DRL, for overall support. Analytical Research Department of Discovery Research SBU is especially acknowledged for providing us with the data to characterize all the compounds.

Notes

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.