Routes to the synthesis of 2-exo- and 2-endo-acryloyloxy-N-(1-adamantyl)bornane-10-sulfonamide have been developed, and preliminary applications of the former as a chiral Baylis–Hillman substrate have been explored.
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Yields and % d.e. obtained for the diastereomeric Baylis–Hillman products were:- 13a (93%, 38% d.e.); 13b (99%, 22% d.e.); 13c (93%, 60% d.e.); 13d (98%, 95% d.e.); and 13e (89%, 52% d.e.).
