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One-pot synthesis of chiral dehydroproline esters: [3+2]-type cycloaddition reaction of allenylstannane and α-imino ester
Authors:Kohei Fuchibe
Institution:Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan
Abstract:An enantioselective 3+2]-type cycloaddition of allenylstannane and α-imino ester was developed. Synthetic utility of the 4-stannyldehydroproline ester intermediate was demonstrated: iodine oxidation and Stille coupling reaction of the intermediate afforded optically active 4-iodo- and 4-aryldehydroproline esters in good yields and in high ees, respectively.
Keywords:Allenylstannane  Annulation  Asymmetric synthesis  α-Imino ester  Iodine oxidation  Proline  Stille coupling
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