1-Iodo-1-selenoalkenes as versatile alkene 1,1-dianion equivalents. Novel connective approach towards the tetrahydropyran subunit of polycavernoside A
(2006) Tetrahedron — Vol. 62, n° 10, p. 2331-2349 (2006)
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- Abstract
- syn-Hydroalumination of 2,4,6-triisopropylphenylselanyl-1-alkynes with DIBAL-H followed by AI/I exchange with 1, afforded exclusively (E)-1-iodo-1-selenoalkenes in good yields. 1-Iodo-1-selenopropene 10 proved to be a convenient 1.1 dianion equivalent, leading to the stereodivergent synthesis of allylsilanes (Z)-6 and (E)-6. Adduct 3, an intermediate in the synthesis of the tetrahydropyran subunit of polycavernoside A, was efficiently synthesised from allyisilane (Z)-6 and aldehyde 7 via an intramolecular Sakurai cyclisation. (c) 2005 Elsevier Ltd. All rights reserved.
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Perez-Balado, C., & Marko, I. (2006). 1-Iodo-1-selenoalkenes as versatile alkene 1,1-dianion equivalents. Novel connective approach towards the tetrahydropyran subunit of polycavernoside A. Tetrahedron, 62(10), 2331-2349. https://doi.org/10.1016/j.tet.2005.12.005 (Original work published 2006)