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Intramolecular cyclizations of allyl- and propargylsilanes

✍ Scribed by Dieter Schinzer; Sándor Sólyom; Marion Becker

Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
217 KB
Volume
26
Category
Article
ISSN
0040-4039

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✦ Synopsis

Allylsilanes of type 2 and propsrgylsilanes of type E undergo efficient cvclizations uoon treatment with EtAlCl_ in toluene to afford stereoselectively functionalized hydrinhanones of type 5 and spiro[4,5]decanes of type 14. -We have recently reported a new stereoselective route to functionalized spiroketones using Lewis acid-catalized cyclizations of allylsilanes.' In connection with other studies we required convenient syntheses of functionslized cis-fused hydrindanones and spiro[4,5]decanes containing the allene functionality. The synthesis for compounds 1 was carried out using 3-ethoxy cyclohexenone (1) as starting material, which was alkylated at -78OC with LDA as base. Treatment of 2 with either LiA1H4, MeLi or EtLi led to compound 2 which was selectively ozonized using Sudan Red as indicator.'

Compound 2 yielded the desired allylsilane 2 after reaction with the Seyferth-Fleming ylid.

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## Abstract Cyclization of the chiral imino lactones with allylic or propargylic groups required acidic conditions to afford spirocyclic (II) or (XII).