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

Autor:	Carlos Perez‐Balado, István E. Markó
Rok vydání:	2006
Předmět:	chemistry.chemical_classification Chemistry Alkene Stereochemistry Protein subunit Organic Chemistry General Medicine Tetrahydropyran Biochemistry Aldehyde Adduct chemistry.chemical_compound Equivalent Intramolecular force Drug Discovery Carbanion
Zdroj:	Tetrahedron. 62:2331-2349
ISSN:	0040-4020
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::7e5c62773ddce9da5fe6358e4400acdf https://doi.org/10.1016/j.tet.2005.12.005 Zobrazit plný text záznamu Full Text from ScienceDirect