Synthetic Communications p. 151 - 164 (2006)
Update date:2022-08-17
Topics:
Bhuniya, Debnath
Gujjary, Srinivas
Sengupta, Sujata
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 (R 3 and EWG). Copyright Taylor & Francis LLC.
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