•Novel domino Michael/retro-oxa-Michael/Michael/Aldol condensation reaction.•Construction of optically pure polyfunctionalized cyclohexene-carbaldehydes.•Double use of the starting aldehyde substrate.A novel domino Michael/retro-oxa-Michael/Michael/Aldol condensation reaction was developed via the reaction of 3-(benzyloxy)propanal with β-nitroalkenes catalyzed by secondary amine. Using this methodology, optically pure polyfunctionalized cyclohexene-carbaldehydes were prepared straightforwardly from two simple starting materials in good yield with excellent stereoselectivity.Download high-res image (121KB)Download full-size image

Valuable chiral N-Boc-β-benzyl-β-amino acid was concisely synthesized via construction of chiral N-Boc-3-benzyl-5-oxoisoxazolidine through cross-metathesis/conjugate addition/oxidation. All of the starting materials for the synthesis of chiral N-Boc-β-benzyl-β-amino acid are cheap, and two-step short procedure make it easy for the rapid construction of various chiral β-arylmethyl-β-amino acids and important drugs, such as sitagliptin phosphate.Valuable chiral N-Boc-β-benzyl-β-amino acid was concisely synthesized via construction of chiral N-Boc-3-benzyl-5-oxoisoxazolidine through cross-metathesis/conjugate addition/oxidation. All of the starting materials for the synthesis of chiral β-benzyl-β-amino acid are cheap, and two-step short procedure make it easy for the rapid construction of various chiral β-arylmethyl-β-amino acids and important drugs, such as sitagliptin phosphate.