Enantioselective Cyclopropanation of 2‐Cyano‐3‐arylacrylates Using Carbohydrate‐based Crown Ethers

Enantioenriched, highly functionalized cyclopropane derivatives were prepared by a simple and green approach using monosaccharide-based chiral crown ethers as phase transfer catalysts. The Michael-initiated ring closure (MIRC) reactions of diethyl bromomalonate with 2-cyano-3-phenylacrylate took place complete diastereoselectivity in the presence lariat derived from carbohydrates enantioselectivity up to 87 % ee was achieved. Among catalysts tested, monoaza-15-crown-5 ether having methyl β-d-glucopyranoside unit 2-(3,4-dimethoxyphenyl)ethyl group on nitrogen generated highest asymmetric induction (87 ee). In analogous 2-cyano-3-arylacrylates, range 8–91 ee.