TY - JOUR AU - Adeyemi, Ahmed; Wetzel, Alexander; Bergman, Joakim; Brånalt, Jonas; Larhed, Mats TI - Regio- and Stereoselective Synthesis of Spirooxindoles via Mizoroki–Heck Coupling of Aryl Iodides SN - 0936-5214 SN - 1437-2096 PY - 2019 JO - Synlett JF - Synlett LA - EN VL - 30 IS - 01 SP - 82 EP - 88 ET - 2018/12/04 DA - 2018/12/14 KW - spirooxindoles KW - Mizoroki–Heck KW - cyclization KW - carbonylation AB - A method for highly regio- and stereoselective intramolecular Mizoroki–Heck 5-exo cyclization of aryl iodides to the corresponding spirooxindoles has been developed. Electron-rich and electron-deficient aryl iodide precursors were selectively ring-closed with high stereoselectivity and good yields. The double-bond position in the cyclopentene ring was controlled by careful choice of reaction conditions. These rare spiro compounds were further functionalized to rigidified unnatural amino acid derivatives by a subsequent gas-free Pd(0)-catalyzed alkoxycarbonylation, followed by selective O- and N-deprotections. PB - © Georg Thieme Verlag DO - 10.1055/s-0037-1611360 UR - http://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0037-1611360 ER -