Sasirome Racochote

Introduction Click to copy section linkSection link copied! Benzoxazin-4-one derivatives represent an important class of compounds in medicinal chemistry with a broad spectrum of biological activities (Scheme 1A). (1) For instance, cetilistat, a clinically used pancreatic lipase inhibitor for obesity management, (1c) as well as reported HSV-1 protease inhibitors (1d) and compounds exhibiting cytotoxicity against P388 leukemia cells, (1e) contain benzoxazinone motifs.

Buy Article Permissions and Reprints All articles of this category Upon treatment of chiral β-trifluoromethyl-α,β-unsaturated N-acylated oxazolidin-2-ones with a range of alcohols using phosphazene base as a catalyst, the unexpected cascade esterification/stereoselective aza-Michael addition was observed. The reactions proceeded with high diastereoselectivities (up to >99:1) to give a series of enantioenriched aza-Michael addition products in good to high yields.

Base-catalyzed diastereodivergent thia-Michael addition to chiral β-trifluoromethyl-α,β-unsaturated N-acylated oxazolidin-2-ones Base-catalyzed diastereodivergent thia-Michael addition of thiols to chiral β-trifluoromethyl-α,β-unsaturated N-acylated oxazolidin-2-ones is reported. By tuning the base-catalyst (i-Pr2NEt, DABCO, or P2-t-Bu), a range of chiral thia-Michael adducts was synthesized in good yields with high diastereoselectivity.