1-Iodo-1-selenoalkenes as versatile alkene 1, 1-dianion equivalents. Novel connective approach towards the tetrahydropyran subunit of polycavernoside A

C Pérez-Balado, IE Markó

Index: Perez-Balado, Carlos; Marko, Istvan E. Tetrahedron, 2006 , vol. 62, # 10 p. 2331 - 2349

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Citation Number: 14

Abstract

syn-Hydroalumination of 2, 4, 6-triisopropylphenylselanyl-1-alkynes with DIBAL-H followed by Al/I exchange with I2 afforded exclusively (E)-1-iodo-1-selenoalkenes in good yields. 1- Iodo-1-selenopropene proved to be a convenient 1, 1 dianion equivalent, leading to the stereodivergent synthesis of allylsilanes and. Adduct, an intermediate in the synthesis of the tetrahydropyran subunit of polycavernoside A, was efficiently synthesised from allylsilane ...