An operationally simple and efficient strategy for a highly potent Dipeptidyl Peptidase-4 (DPP-4) inhibitor, sitagliptin has been developed employing readily available precursors. The chiral b-amino acid core of sitagliptin has been constructed through a Barbier type allylation of chiral sulfinyl imine or a Mannich type addition of diethyl malonate. This approach is more convenient, exquisitely selective and practical.

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Racemic syn‐ethyl (E)‐2‐(2,2‐dimethyl‐6‐styryl‐1,3‐dioxan‐4‐yl)acetate is hydrolyzed with high enantioselectivity by Novozyme‐435 in 0.05 m sodium phosphate buffer at room temperature. The optically pure unreacted ethyl 2‐((4R,6S)‐2,2‐dimethyl‐6‐((E)‐styryl)‐1,3‐dioxan‐4‐yl)acetate and hydrolyzed (4S,6R)‐acid are used in the synthesis of HMG‐CoA reductase inhibitor rosuvastatin and the naturally occurring styryl lactone cryptomoscatone E1, respectively.