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| - Nonenzymatic Acylative Kinetic Resolution ofBaylis−Hillman Adducts
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| Abstract
| - The first efficient nonenzymatic acylative kinetic resolutionof Baylis−Hillman adducts is reported. Chiral pyridinecatalyst 1a and an optimized analogue 1e are capable ofpromoting the synthetically useful enantioselective acylation(the efficiency of which is outstanding for sp2−sp2 carbinolsubstrates, s = 3.5−13.1, ee up to 97%) of Baylis−Hillmanadducts derived from recalcitrant precursors which arecurrently difficult to synthesize utilizing benchmark asymmetric Baylis−Hillman reaction catalyst technology. A novelone-pot synthesis−kinetic resolution process involving aDBU-catalyzed Baylis−Hillman reaction and subsequent 1e/DBU-mediated enantioselective acylation has also beendeveloped.
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